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When Darrick Ramsey first held the single dollar bill he’d been given, anxiety hit him hard. “I was very nervous, like I was anxious,” he recalls in an interview with Entrepreneur. 

Alexis Jordan had a similar reaction: “For me, I was very nervous,” she says. 

In February 2024, a documentary film team tasked these two students, along with about two dozen of their then-high school classmates, with an unusual challenge: Turn $1 into $100 in a week using all of the resources at their disposal. They started the challenge terrified of failing, then used their businesses, networks and hard work to turn $1 into far more than $100 in a week. A documentary film released last month called Learn to Earn: A Student’s Journey From $1 to $100 chronicled their experiences.

Both Ramsey and Jordan initially grappled not just with the math, but with the reality of trying to build something in “this economy,” as Jordan put it, where “what can you get for $1?” is a genuine question. The time frame added pressure: They had roughly a week, layered on top of school, sports and other commitments, to turn $1 into $100. “We had other stuff to do, so it was very time-consuming,” Jordan says. 

How Jordan flipped $1: services and Kool-Aid pickles

Once the shock of the $1 challenge wore off, Jordan went directly to the community she knew best. “My strategy was, where do people give the most money?” she says. “So for me, I was raised in a church; my church is like a big family. So I said, let me go to my number one supporters.” With that single dollar and her existing relationships, she offered labor and creativity instead of products she couldn’t afford to buy.

“Usually what I did was I cleaned their yards, I cleaned the church,” she says, describing how she exchanged services for donations and payments.

Then she layered on a homemade snack that became an unexpected hit: Kool-Aid pickles.

“It’s weird,” she says. “But a lot of people bought them. Everybody bought them, like everybody was going crazy over them.”

She explained the process simply: “You get the pickle jar, you pour out the pickle juice and then you just mix Kool-Aid packets and sugar with it, and then pour it back and let it ferment in the refrigerator for like a day or two, and then after that you put them in a Ziploc bag and you just sell them.”

With cleaning work for local small businesses and a snack that turned heads, she surpassed the $100 target.

Where she is now

More than two years later, Jordan, 19, runs a business called Blended Threads LLC, which centers on childhood diabetes, a condition she was diagnosed with in fourth grade.

She wrote a children’s book, Why Did Diabetes Pick Me, chronicling her struggles and how she overcame them. She is now working on a second book, this time a chapter book. She’s also a keynote speaker, turning her lived experience with juvenile diabetes into education and advocacy. 

“I wanted to broadcast and bring awareness to it, because you rarely hear anybody talk about childhood diabetes or juvenile diabetes,” she says, adding that people in her community were “shocked” to learn more and “glad” she published the book.

For Ramsey, the turning point came when he realized that the $1 was less important than the relationships he already had. He was part of the CEO program at his high school, and the program had taken students to tour businesses in the community. 

“We had a journal, and I wrote down each business owner, their name and their contact,” he says. When the $1-to-$100 challenge arrived, he asked himself: Why can’t I just reach back out to these guys to see if they can help me?

He recorded a simple one-minute video for those contacts: “I tried to keep it real short and simple, explaining, hey, my name is Darrick Ramsey. I talked to you in the CEO program before. I’m just wondering if you had any advice or if I can pressure wash your car or detail it for you,” he says. 

He had bought the power washer before the challenge with money from an hourly job.

The response was overwhelming. “I kind of overbooked myself with all the people that we had met and all the people they know,” he says. “I really got to see the community coming together. It was just great.”

He focused first on pressure washing and later added car detailing as demand grew. “It got to the point where I had to pressure wash in the cold, had to pressure wash in the rain; we had the car detail in the freezing cold, like cars were icing over as we were washing them,” he says, describing one of the busiest weeks of his life. By the end of the challenge, he’d far exceeded the target, earning $2,065. 

Where he is now

Ramsey, 20, was born in Decatur, Alabama, and moved between Chicago, Atlanta and Alabama before settling back in Decatur. He struggled “academically, financially” in school, which shaped his purpose now: “I feel like one of my life’s purposes has been trying to help the youth with what they do best, and keep excelling,” he says. He is a physical education teacher and mentor who “goes all over Decatur city schools” to connect with kids, pulling them aside to talk through “behavior issues and really just stuff I was struggling with.”

His business, PeerPressure, was born out of personal grief and bad influences in middle and early high school. After a close friend died the summer before ninth grade, he says, “I was peer-pressured into doing a lot of things that I really felt like I wouldn’t have done if I wasn’t around those bad friends.” 

In his sophomore year, with the help of teachers, he turned that story into a brand. PeerPressure now offers pressure washing, mobile car detailing, house washing and automotive light work, built over “about four years” and expanded through work with “many business owners within our community and outside of our community,” he says. 

His biggest challenge was internal

Ramsey says that he was his own “biggest enemy” solely because he didn’t really believe in community or family at the time. Academic and financial struggles left him feeling isolated and under pressure, which “created a lot of self-doubt” during that week.

Reaching out to people changed that perception. “They started showing me that I wasn’t alone,” he says. “Then I started to see a bigger vision.”

The lesson has stayed with him. He endured years of “long nights, a lot of crying, a lot of work.” Those years helped him define his purpose: “If I can change somebody’s life through teaching and mentoring, then I feel like I’ve fulfilled my purpose,” he says. 

This article is part of our ongoing Young Entrepreneur® series highlighting the stories, challenges and triumphs of being a young business owner.

When Darrick Ramsey first held the single dollar bill he’d been given, anxiety hit him hard. “I was very nervous, like I was anxious,” he recalls in an interview with Entrepreneur. 

Alexis Jordan had a similar reaction: “For me, I was very nervous,” she says. 

In February 2024, a documentary film team tasked these two students, along with about two dozen of their then-high school classmates, with an unusual challenge: Turn $1 into $100 in a week using all of the resources at their disposal. They started the challenge terrified of failing, then used their businesses, networks and hard work to turn $1 into far more than $100 in a week. A documentary film released last month called Learn to Earn: A Student’s Journey From $1 to $100 chronicled their experiences.

Most entrepreneurs never fail. They simply stop too early. They build a business that provides a living, then spend years operating it without ever scaling it into a true asset. They create income but not enterprise value.

Looking back on my own career, I can divide entrepreneurship into three distinct phases: Build. Scale. Dominate.

Understanding the difference changed everything.

Build

Building a viable business is a worthy goal, and many people attempt it. Some succeed.

This is the stage where entrepreneurs learn how to sell. Just as Calculus 1 eliminates many aspiring engineers, sales eliminates many aspiring entrepreneurs. It is the first great test of business ownership.

In the build phase, revenue is king. We do whatever it takes to get revenue through the door and then figure out how to turn it into profit. The focus is almost entirely on the profit and loss statement because no business can survive if it consistently loses money.

Early in my investment advisory career, I was fortunate to receive some support while learning the sales process. I worked for a large brokerage firm in downtown Washington, D.C., where I partnered with a senior advisor. He handed me a list of smaller client accounts and told me, “It’s up to you to turn chicken sh!t into chicken salad.”

For the next several years, I learned how to persuade, retain and serve clients — mostly over the phone.

I never became one of the elite producers in the office, but I became good enough to go independent. Suddenly, I had what many entrepreneurs dream about: a business with no boss.

I also discovered what many entrepreneurs eventually learn: A business without a boss still has problems.

Some clients followed me when I left. Many did not. What had started as a process of learning a new profession became a marketing challenge. Looking back, I did not yet understand the power of positioning, niche specialization or an irresistible offer. I had built a practice, but I had reached a plateau.

At the same time, I was wrestling with the realities of self-employment. Revenue growth was difficult, taxes were higher than expected, and progress felt slow. This became the grinding phase of my career. I tried many things. Most failed.

Scale

Building creates income. Scaling creates assets.

Scaling is the transition from operator to owner. It transforms a job with no boss into a business with value beyond the owner’s daily efforts. It also changes how you think. Instead of focusing exclusively on the income statement, you begin building both business and personal balance sheets.

Of the two problems I faced — marketing and taxes — it was taxes that I solved first.

Through the teachings of Sandy Botkin, CPA and attorney, I immersed myself in the world of small business tax strategy. I learned about entity structures, retirement plans, expensing opportunities and other tools available to business owners. Over time, I became proficient enough to improve my own financial position and eventually help others do the same.

Ironically, what began as an effort to improve my investment advisory business led me somewhere unexpected.

I had been encouraged to build referral relationships with tax professionals. The idea was simple: Exchange referrals and grow together. While that strategy produced limited results, it exposed me to an entirely different opportunity.

I earned my IRS Enrolled Agent credential and launched a tax practice. What I thought would become a marketing solution became a scaling opportunity.

As I discussed in a previous article, I used debt to accelerate that growth. I acquired two tax practices from retiring owners. Unlike the investment advisory business, where acquisitions can be difficult and heavily regulated, opportunities in the tax profession were abundant.

I wasn’t really buying businesses. I was buying cash flow. The client relationships, recurring revenue and enterprise value came with it.

The acquisitions worked well and allowed me to scale far more rapidly than organic growth alone would have permitted.

The next scaling opportunity came through real estate.

After leasing office space, I explored purchasing the building I occupied. When that opportunity did not materialize, I purchased a commercial condominium in a new development. Once again, I used debt — but this time to acquire a different asset.

Instead of buying cash flow, I bought real estate.

Banks love lending against real estate. My tax business became the best tenant I will ever have. The arrangement created tax advantages, increased control over my workspace and added another asset to the balance sheet.

For the first time in my entrepreneurial journey, I was no longer focused solely on generating revenue. I was building assets that could appreciate, produce income and create long-term wealth.

I had finally moved beyond building. I was scaling.

Dominate

The final phase is domination.

Dominate does not mean eliminating competitors. It means becoming the obvious choice for a specific market.

It is characterized by:

• A clearly defined niche market with strong demand
• Exceptional product or service delivery
• A reputation that generates referrals and trust
• Systems and processes that support growth
• Some form of moat that makes client attrition less likely

The dominate phase began when we discovered a niche within the Snap-on franchise community.

Like many successful niches, it was not something I intentionally set out to find. It emerged through experience. As our client base grew, I noticed that Snap-on dealers shared a unique set of challenges. Their bookkeeping is more complex than that of many small businesses due to inventory management, route operations, financing arrangements and the industry’s unique reporting requirements. Generic accounting knowledge was often insufficient.

The niche also presented a marketing challenge. Most Snap-on franchisees spend their days serving customers, managing inventory and operating their routes. They are rarely sitting at a desk consuming business content or scrolling social media. Reaching them required a different approach.

Equally important, I found that I genuinely enjoyed working with them. Having grown up in a blue-collar environment, I understood many of their values and experiences. We spoke a similar language. Trust developed naturally.

Over time, specialization created momentum. As our expertise deepened, referrals increased. Marketing became easier. Prospective clients were no longer looking for a tax preparer. They were looking for someone who understood their business.

That is what domination looks like.

It is not about eliminating competitors. It is about becoming the obvious choice for a specific group of people with a specific problem. When that happens, the grind of constantly chasing prospects begins to fade. Reputation starts doing much of the heavy lifting.

The business gains a moat. Clients stay longer. Referrals become more frequent. Enterprise value grows.

Most entrepreneurs focus on building. Some learn how to scale. Very few reach the point where their market actively seeks them out.

That is the power of domination.

Many entrepreneurs spend their entire careers in the build phase. They learn how to generate revenue but never learn how to create enterprise value.

The opportunity is not simply to build a business. The opportunity is to build it, scale it and ultimately become the dominant solution for a specific market.

Revenue creates income. Scale creates wealth. Dominance creates options.

Most entrepreneurs never fail. They simply stop too early. They build a business that provides a living, then spend years operating it without ever scaling it into a true asset. They create income but not enterprise value.

Looking back on my own career, I can divide entrepreneurship into three distinct phases: Build. Scale. Dominate.

Understanding the difference changed everything.

There’s a line you hear in a lot of leadership talks: “People don’t leave companies, they leave managers.”

In a hybrid company, however, this can play out a little differently. People leave managers who stop being able to read them. The instincts that work in an office don’t always translate well across a dozen screens and different time zones, and plenty of good managers might not even notice until it’s too late.

When I started building BriteCo, I assumed the hard part of leading a distributed team would be the logistics. However, the actual challenge was relearning how to connect with people. It’s emotional work, and the screen backgrounds and mute-button etiquette we tend to fixate on barely scratch the surface. Most of us were never trained for the kind of leadership that hybrid work actually demands.

The hallway moved, so I had to move with it

One of the most underrated things about an office is its hallway. Someone walks past your door with a half-formed question, you talk for 20 minutes and a problem you’d both been circling for a week is suddenly solved. We’ve experienced that at BriteCo more times than I can count.

However, this type of spontaneous interaction just doesn’t happen on its own when half the team is remote. So, we stopped waiting for it to happen naturally and started manufacturing it. We keep a few Slack channels dedicated solely to unfinished ideas with no set agenda. We also schedule virtual coffee breaks on the calendar with no connection to any project. Our in-office days are now reserved for messy, collaborative work, with focused work taking place wherever a person actually concentrates best.

These practices give creative energy somewhere to land, even if they never fully recreate the hallway.

Most of my cues don’t survive a screen

It’s genuinely hard to read a room over video. The signals I used to rely on — a shift in posture or the atmosphere going flat when an idea lands wrong — are often muted or absent on a call.

To tackle this issue, I’ve become more direct. I ask people how they’re actually doing, then I stay quiet and wait for the real answer instead of the default “good, busy” response. I also ask what frustrated them this week. I used to treat these questions as optional, but they serve a valuable purpose. For a leader who can’t rely on physical presence, they help you collect the information that the hallway used to hand you for free.

I run a jewelry insurance company, so I spend my days thinking about objects that carry enormous emotional weight for the people who own them. An engagement ring is never just a ring. That sensitivity to what something means to a person has to extend inward to the team; otherwise, it’s just a talking point in a brand presentation.

Trust does the work the office used to do

For a long time, many managers relied on a lazy shortcut: if I can see you at your desk, you must be working. The reality is that some people do coast when no one is watching. However, plenty of others do their best work at home with no commute, fewer distractions and a closed door. Desk visibility never told you which employee was which, so you never found out.

Trust-based leadership replaces that shortcut, but it demands more from you on both a psychological and professional level. You have to know each person on your team well enough to understand what conditions allow them to do their best work. The warning signs also need to be caught earlier, because the casual observations that once revealed them are gone. That also means having difficult conversations sooner, before problems have time to grow.

At BriteCo, culture is created deliberately rather than inherited. We run off-site and all-hands gatherings, and we stay rooted in Evanston, where our relationship with Northwestern University has helped build a strong talent pipeline that keeps us tied to the place we’re from. We prioritize clear and frequent communication across our online channels, too, so that our remote workers never feel disconnected or isolated from their colleagues who do come into our offices. Our local roots and hybrid model work in tandem, enabling us to offer flexible working to our team. 

The managers who succeed in this new hybrid work environment are the ones who can sense how someone is doing through a screen and build trust without needing to see them in person. Better software and stricter return-to-office policies won’t get you there; it’s a skill that needs practice and a framework we’re always working to improve. Over time, I’ve found that getting better at reading people I can’t see has made me more attuned to those sitting right across the table from me.

There’s a line you hear in a lot of leadership talks: “People don’t leave companies, they leave managers.”

In a hybrid company, however, this can play out a little differently. People leave managers who stop being able to read them. The instincts that work in an office don’t always translate well across a dozen screens and different time zones, and plenty of good managers might not even notice until it’s too late.

When I started building BriteCo, I assumed the hard part of leading a distributed team would be the logistics. However, the actual challenge was relearning how to connect with people. It’s emotional work, and the screen backgrounds and mute-button etiquette we tend to fixate on barely scratch the surface. Most of us were never trained for the kind of leadership that hybrid work actually demands.

You did everything right. You invested in AI early, ran pilots, got board approval and committed real budget to an AI-first strategy. So why is the ROI still so hard to prove?

In the past few years, one problem has come up in nearly every executive conversation I’ve had: AI technical debt. Not the definition your engineering team uses internally, but the business cost behind it. Shortcuts taken to get AI tools running faster, integrations bolted onto systems never designed for them and pilots that shined in demos but needed constant fixes in production all compound into a cost that’s now eating into every AI dollar you spend.

IBM’s Institute for Business Value puts a number on it: enterprises that ignore technical debt see AI project ROI drop by 18% to 29%. That’s the money spent maintaining, patching and working around problems that shouldn’t have existed in the first place. And 81% of the executives IBM surveyed said technical debt is already constraining their AI success.

Why AI debt compounds faster than any tech debt before it

Technical debt has been around since the first developer took a shortcut to meet a deadline. But AI debt plays by different rules, and I’ve watched it catch leaders off guard in new ways.

Traditional tech debt sits still: old codebases, outdated servers, systems that haven’t been touched in years. AI debt moves. The prediction model that worked well in January starts producing unreliable results by June because real-world conditions shifted and no one scheduled a retraining cycle. The integration your team built between your CRM and your AI analytics tool breaks every time either system updates. Each fix looks minor on its own, but twelve months of minor fixes add up to a budget line nobody planned for.

Then there’s the vendor problem. Gartner predicts more than 40% of agentic AI projects will be canceled by the end of 2027, citing escalating costs and unclear business value. One reason: the market is saturated with what Gartner calls “agent washing,” vendors rebranding chatbots as AI agents. Of the thousands of agentic AI vendors, Gartner estimates only about 130 offer genuine capabilities. If you’ve been buying based on demos and pitch decks, it’s worth asking your team whether what you purchased really qualifies.

Four signs your AI investment has a debt problem

Here are four patterns I see repeatedly when talking to executives who invested early in AI but can’t explain the returns.

1. Your AI tools work in demo but underperform in production. This is the most common complaint I hear. The pilot looked impressive in the boardroom. Six months later, your team is spending more time maintaining the system than using it. If your AI line items are growing but the business outcomes aren’t, that gap is the tax.

2. You’re paying for multiple AI tools that do overlapping things. Marketing bought one platform. Operations bought another. Finance is trialing a third. None of these purchases was coordinated. Now you have five tools that don’t communicate with each other, a monthly bill that keeps climbing and no single person who can map out what they all do. This kind of uncoordinated tool purchasing is one of the fastest-growing hidden costs I see.

3. Your data team spends more time cleaning than analyzing. Every AI system runs on data, and if your data infrastructure wasn’t ready before you layered AI on top, every project is building on a weak base. I’ve seen companies spend six months on an AI initiative only to realize the real problem was the quality of the data feeding it. My advice: ask about data readiness before you sign the AI contract, not after.

4. You can’t explain your AI ROI to your board. This one matters most because no technology team can fix it for you. If the value feels vague, the governance probably doesn’t exist. Deloitte’s 2026 State of AI in the Enterprise report found that only one in five companies has a mature model for governing autonomous AI agents. No governance means no measurement, which leaves you in front of the board with a number you can’t defend.

Three moves worth making before your next AI investment

If any of those signs sound familiar, here’s what I’d recommend.

Audit before you add. Before signing your next AI contract, ask one question: can our current infrastructure support this without creating new debt? If the answer is vague, that tells you everything you need to know. The biggest mistake I see is treating AI as a technology purchase. PwC’s 2026 AI predictions research reinforces that technology delivers only about 20% of an AI initiative’s value. The other 80% comes from redesigning how the work gets done, and CTOs can’t do that alone.

Cut the projects that aren’t delivering. Ask for a list of every AI proof-of-concept currently running, what each one costs per month and what measurable business outcome it produces. If that third column is mostly blank, those are the ones to cut. Shut them down and redirect those resources toward the two or three initiatives with a realistic path to production value.

Modernize before you layer. This is the advice that sounds least exciting but produces the biggest returns. At Accedia, the projects where AI actually delivered on its promise had one thing in common: the client invested time in fixing their infrastructure before introducing AI. In a recent case, we spent eight weeks retiring outdated data components and restructuring their systems. When we introduced AI after that, deployment reached production 30% faster than their previous attempts, because it was built on a foundation that could support it.

Where the real returns are

The next time someone asks you to justify your AI spend, don’t reach for another dashboard or vendor pitch. Look at what’s underneath. The only way to see real AI returns over the next 18 months is to fix what’s broken before investing in what comes next.

You did everything right. You invested in AI early, ran pilots, got board approval and committed real budget to an AI-first strategy. So why is the ROI still so hard to prove?

In the past few years, one problem has come up in nearly every executive conversation I’ve had: AI technical debt. Not the definition your engineering team uses internally, but the business cost behind it. Shortcuts taken to get AI tools running faster, integrations bolted onto systems never designed for them and pilots that shined in demos but needed constant fixes in production all compound into a cost that’s now eating into every AI dollar you spend.

IBM’s Institute for Business Value puts a number on it: enterprises that ignore technical debt see AI project ROI drop by 18% to 29%. That’s the money spent maintaining, patching and working around problems that shouldn’t have existed in the first place. And 81% of the executives IBM surveyed said technical debt is already constraining their AI success.

Across two decades, I’ve held twelve corporate roles of increasing responsibility and scope. Some came with positional power and authority. Some did not. At the end of the day, it didn’t matter when it came to my ability to make an impact and advance my career.

The reality is you’re not always going to be the boss with decision rights, but you can always be a leader. In fact, the higher I climbed, the more often I found myself leading cross-functional initiatives that required buy-in from other teams and approval from senior stakeholders.

What I learned along the way is that influence, not authority, is what drives real progress. You don’t need permission to become an excellent leader, just the right mindset and relationships.

Leadership is about relationships, not rank

No matter your title, cultivating influence in an organization starts by building strong relationships in order to solve problems. This way, you will naturally gain allies who are willing to follow your lead. Not because they have to. But because they want to.

I’ve found that the most powerful influence you can earn stems from self-awareness. For example, knowing when to give up short-term decision rights to build a better long-term relationship. Trust me, your willingness to be flexible will be remembered in future interactions.

On the topic of decision-making, the biggest mistake I see people make when “acting like a leader” is to attempt to hold on to all decision rights simply because they are the most senior person on a project, not because they have the most knowledge. Don’t fall into this trap.

A self-aware leader knows who in the room is the most knowledgeable on a topic, and then will allow them to own related decisions. This not only results in better project outcomes but builds trust.

Here are a few more tips for becoming more self-aware as a leader to drive influence:

• Admit if you are not prepared to make an informed decision and ask for clarification.
• Invite others into the decision-making process if you lack experience or knowledge.
• Seek out context and potential cross-functional impact before making a decision.

The best way to build credibility with peers and senior leaders

Instead of trying to prove yourself at the start of a large project, commit to learning. The first 30 days should be spent understanding the landscape. Meet with stakeholders. Ask questions to understand their priorities, concerns and how this project will impact their team.

Most importantly, determine who has final decision rights to avoid confusion and setbacks. By the end of these conversations, I try to have clarity in three areas:

• How the project impacts each department.
• Who has decision rights.
• Where alignment and misalignment exist.

What to do when roles are unclear on a cross-functional project

Cross-functional projects are rarely neat and organized at the beginning. Often, responsibilities overlap, and ownership over decisions rights isn’t yet defined.

In these situations, leadership is about creating clarity. Here’s how to gain momentum:

• Schedule a cross-functional workshop to build a shared timeline for completion with key milestones. There should be at least one representative from each team present.
• Require workshop participants to share back information with respective teams to get feedback and bring it back to your workshop group if anything was missed initially.
• Present the project’s finalized roadmap highlighting all key milestones to leadership to determine decision rights for each one, alignment of resources, and finalize a timeline.

Influencing outcomes through collaboration: a case study

I was once responsible for launching an entirely new brand, tasked first with developing a product description and instructions on how to use it. All this information had to come together on the packaging, a process that required close collaboration with highly specialized teams focused on medical, legal and regulatory requirements — none of which reported to me.

Even in the earliest stage of the project, I knew every packaging decision would ultimately shape how I could market, educate and talk to consumers about the brand later down the road. Yet, I had no formal authority over the teams making the calls, so here’s what I did:

First, I tackled an often overlooked (yet simple to solve) hurdle that can stunt collaboration: proximity. These specialized teams physically worked on the other side of the building, so I made the decision that, for half of the week, I would physically go and sit with them. Even if I was working on something unrelated to our project, I was intentional about being present and available.

As the weeks progressed, this choice led to team members casually calling me into hallway conversations about our packaging simply based on proximity. It also allowed me to listen and learn from those teams on how they work and what was driving their decisions.

By inserting myself in their world, I also had the opportunity to chime in to explain our marketing strategies and give broader context regarding consumers. Ultimately, this allowed us to jointly build a packaging recommendation that met all medical, legal and regulatory requirements while still giving the marketing team plenty of room to promote the brand effectively.

The bottom line on influence vs. authority

No, your title does not dictate how much influence you can have within an organization. But it should impact how you go about earning it. Cultivating influence always comes back to self-awareness, whether that means deferring to someone with less authority but more expertise to build trust or leading with curiosity, not control, as a newcomer to a project.

When people see you taking time to understand their perspective and create alignment, trust begins to form naturally and they will be more willing to support your recommendations.

Across two decades, I’ve held twelve corporate roles of increasing responsibility and scope. Some came with positional power and authority. Some did not. At the end of the day, it didn’t matter when it came to my ability to make an impact and advance my career.

The reality is you’re not always going to be the boss with decision rights, but you can always be a leader. In fact, the higher I climbed, the more often I found myself leading cross-functional initiatives that required buy-in from other teams and approval from senior stakeholders.

What I learned along the way is that influence, not authority, is what drives real progress. You don’t need permission to become an excellent leader, just the right mindset and relationships.

After more than a decade of bootstrapped growth, Oxylabs is taking outside capital for the first time as the rapid development of AI agents accelerates the growing demand for the web data infrastructure the company has spent years building.

The Lithuania-founded technology company has received a $130 million investment from private equity firm Warburg Pincus, valuing the Oxylabs group at $3.6 billion. The deal places Oxylabs among Lithuania’s highest-valued technology companies and gives the business additional capital to expand its data platform as AI developers build systems that increasingly need access to current information from the open web.

Oxylabs says it has reached $350 million in annual recurring revenue and its platform is used by more than 350,000 technology teams worldwide. The company has remained bootstrapped since its founding in 2015, making the Warburg Pincus deal a significant change in how it plans to finance its next stage of growth.

“As AI agents begin to navigate the web far more than humans ever have, the future belongs to the data infrastructure that grounds these systems in real-time, interruption-free knowledge,” Oxylabs CEO Vytautas Savickas said.

The timing of the investment is closely tied to the growing infrastructure requirements across data-driven industries and especially surrounding agentic AI. AI models can contain extensive learned information, but agents designed to monitor markets, conduct research, compare products, or complete online tasks need access to information that changes continuously.

That creates a different technical problem from training a model on a large collection of historical data. An agent operating in real time has to navigate websites, retrieve current information, and continue working when the structure of the web changes. As more companies deploy autonomous systems, the number of machine-driven interactions with the internet could increase substantially.

Oxylabs has spent the past decade developing infrastructure for large-scale access to public web data. Its global network handles billions of requests daily, while its products are used across e-commerce intelligence, cybersecurity, travel, brand protection, and other industries where current online information can influence business decisions.

AI is now adding another source of demand to that existing market.

“The next generation of AI won’t be powered by static indexes that only capture yesterday’s internet,” Savickas said. “For it to work at enterprise grade, the infrastructure behind them is key: the scale, speed, reliability, and compliance required to make open-web knowledge usable in real-time production.”

Oxylabs built and is now developing its product portfolio around those requirements, including web index and headless browser technologies intended to support developers building AI agents and other applications that interact directly with the web.

Warburg Pincus is investing as the company looks to expand its infrastructure and strengthen its global network. The private equity firm cited Oxylabs’ technology, compliance practices, and established relationships with large enterprise customers as important parts of the investment case.

“Oxylabs has established itself as a leader in data infrastructure through its sophisticated, robust, and compliant technology and expansive network,” said Allison Ross, principal at Warburg Pincus. “We are excited to support the Oxylabs team as they continue to expand their offering to help their blue-chip customers access and unlock data-driven insights.”

The investment also gives Oxylabs more flexibility to pursue acquisitions and partnerships. The company acquired Webshare Software in 2022 and ScrapingBee in 2025, transactions that expanded its product offering and reach within the developer community.

Oxylabs CFO Jurgis Rudgalvis said the company plans to continue looking for corporate development opportunities that can add technology and products to its broader ecosystem.

The decision to accept outside capital after more than 10 years is notable because Oxylabs had already reached substantial scale without institutional investment. Its revenue results, more than 160 patents, and existing customer base give the company a different starting position from many AI infrastructure businesses raising capital to develop an initial commercial market.

For Oxylabs, the new investment is intended to accelerate an established business as the profile of its underlying technology changes. Web data access has long supported industries that monitor prices, protect brands, investigate threats, and analyze markets. Agentic AI could place similar infrastructure beneath a much larger number of automated applications.

The deal also carries significance for Lithuania’s technology sector. Oxylabs is the second unicorn to emerge from the Tesonet accelerator and, at a $3.6 billion valuation, has become one of the country’s most valuable technology companies and probably the highest-valued one in the history of such web data infrastructure platforms.

“This achievement shows that Europe has the potential to build sovereign, world-class technology that top AI developers depend on,” Savickas said. “At the same time, it is a moment of pride for Lithuania, demonstrating that market-leading companies like Oxylabs can be built by the relentless work of our talents.”

Oxylabs still has to execute on the opportunity created by agentic AI. Developers are experimenting with different approaches to real-time retrieval and browser interaction, while questions around reliability and responsible web data access remain important as automated systems generate greater volumes of activity.

The Warburg Pincus investment gives Oxylabs additional resources to compete as those technical standards develop. It also gives the company its first institutional investor at a point when the infrastructure it has built over the past decade is becoming more closely connected to one of technology’s fastest-growing areas.

Oxylabs did not need outside capital to reach $350 million in recurring revenue. Its decision to raise $130 million now suggests the company believes the market forming around AI agents is large enough to justify changing a funding strategy that worked for more than a decade.

After more than a decade of bootstrapped growth, Oxylabs is taking outside capital for the first time as the rapid development of AI agents accelerates the growing demand for the web data infrastructure the company has spent years building.

The Lithuania-founded technology company has received a $130 million investment from private equity firm Warburg Pincus, valuing the Oxylabs group at $3.6 billion. The deal places Oxylabs among Lithuania’s highest-valued technology companies and gives the business additional capital to expand its data platform as AI developers build systems that increasingly need access to current information from the open web.

Oxylabs says it has reached $350 million in annual recurring revenue and its platform is used by more than 350,000 technology teams worldwide. The company has remained bootstrapped since its founding in 2015, making the Warburg Pincus deal a significant change in how it plans to finance its next stage of growth.

While some entry-level workers struggle to find work amid a tough job market, certain fields are incentivizing young talent to apply with sky-high salaries. 

Wall Street trading firm Susquehanna International Group (SIG) is offering 2027 summer interns $8,600 a week, or $34,400 a month, to work as quantitative traders and quantitative researchers in its New York and Philadelphia offices, per a recent Fortune report. The internship pays $86,000 in total across a 10-week summer program.

Job listings show that SIG is looking for PhD candidates graduating by summer 2026 or postdocs specializing in quantitative fields like mathematics, physics, computer science or economics. Undergraduate interns can still take home up to $7,600 a week, depending on the role. 

Wall Street is known for its long hours and intensity. SIG takes some of the pressure off of interns by providing free housing, two complimentary meals a day and access to social events like poker tournaments. 

It’s difficult to land a Wall Street internship

SIG pays interns far more than other firms pay the typical U.S. worker. According to the U.S. Bureau of Labor Statistics, the median U.S. worker earned about $1,235 per week during the first quarter of this year. They would have to clock in for about two months to earn what PhD SIG interns take home in one week. 

SIG’s intern salaries are noteworthy, but they are just one example of extravagant pay on Wall Street. For example, Jane Street sets summer intern pay at $300,000 annually, or around $5,700 a week. Meanwhile, Citadel interns take home $4,300 to $5,800 per week in base salary. 

These salaries attract considerable interest. Scoring one of these Wall Street internships is difficult; the roles are intensely competitive. It’s easier to get into Harvard than to make it on Wall Street. 

For example, Goldman Sachs boasted an acceptance rate below 1% for the past three years for its intern class. 

“I think the selection rate speaks both to the strength of the opportunity and the caliber of talent we’re attracting globally,” Jacqueline Arthur, Goldman’s head of human capital management, told Fortune last month. 

She added that the firm views hiring its interns as a long-term investment in leadership, with 40% of Goldman’s current partners originating from on-campus recruiting. 

Goldman’s incoming class is diverse. The firm counts high-level athletes, accomplished musicians and nonprofit founders as part of its cohort. The mix indicates that Goldman is seeking more than just quantitatively focused candidates from a narrow set of elite colleges. 

“We’re meeting individuals with a wider range of academic backgrounds, lived experiences and ways of thinking,” Arthur told Fortune. “It allows us to better understand the full person behind the application — and gives candidates a clearer view of the firm and where they might contribute.”

While some entry-level workers struggle to find work amid a tough job market, certain fields are incentivizing young talent to apply with sky-high salaries. 

Wall Street trading firm Susquehanna International Group (SIG) is offering 2027 summer interns $8,600 a week, or $34,400 a month, to work as quantitative traders and quantitative researchers in its New York and Philadelphia offices, per a recent Fortune report. The internship pays $86,000 in total across a 10-week summer program.

Job listings show that SIG is looking for PhD candidates graduating by summer 2026 or postdocs specializing in quantitative fields like mathematics, physics, computer science or economics. Undergraduate interns can still take home up to $7,600 a week, depending on the role. 

Leaders are often really good at looking out in the world around them to find inspiration for their next breakthrough. They scan the market for pain points, potential customers, partnerships, new products and funding opportunities. But inside large, mature organizations, some of the most powerful innovations often start with a founder’s mindset inside the organization.

Internal innovators, often called intrapreneurs, are closest to the work, the friction and the customer experience. When leaders recognize and empower them, those individuals can drive innovation, speed and competitive advantage that competitors struggle to replicate.

I experienced this early in my career at the Kelley School of Business. A colleague named Brad Wheeler pushed ideas that felt bold at the time. He advocated for a laptop requirement for MBA students and encouraged the use of Lotus Notes to enable digital collaboration among students and faculty. That work became an early version of what we now call a learning management system.

Later, when I stepped into a leadership role connected to those initiatives, the groundwork Brad had laid helped launch Kelley Direct, the school’s fully online MBA program, which eventually became the number one online MBA program in the country. None of that would have happened without our dean being a leader willing to bet on an internal innovator, Brad.

Here is how leaders can identify and empower intrapreneurs inside their organizations.

1. Spot the hidden intrapreneurs

Intrapreneurs are usually the people doing the work who see how things could be better.

These individuals tend to share several traits. First, they are knowledgeable about a specific area of the business. Second, they show genuine passion for improving it. And third, they are credible enough that others believe they can pull their ideas off.

They also tend to offer specific improvements instead of vague complaints. Rather than saying something is broken, they explain exactly what should change.

Leaders sometimes miss these people because leadership responsibilities pull attention elsewhere. Finances, partnerships, hiring and customers demand constant focus. Meanwhile, employees closer to the work are developing insights leadership may never hear unless they ask.

Routine check-ins make a difference. Ask questions like: How is the work going? What are you seeing that we might be missing? What would you change if you could? Sometimes the next breakthrough is sitting quietly inside the organization, waiting for someone to ask.

2. Create psychological safety for innovation

Innovation struggles in environments where people are afraid to speak up.

Many organizations say they want innovation, but their culture unintentionally suppresses it. One common reason is leadership insecurity. If leaders feel threatened when challenged on their ideas or processes, employees quickly learn that raising new ideas can create problems instead of opportunities.

Culture can also contribute. When specific results become the only metric that matters, experimentation feels risky. If every unsuccessful attempt is condemned as a failure, employees stop proposing new approaches. Leaders must demonstrate that thoughtful experimentation is valued.

In team meetings, talk openly about initiatives that did not work but produced valuable learning. Recognize when teams tested an idea quickly and gained insight. Celebrate both wins and failures that generated progress. Leaders should also respond constructively when someone raises a concern or proposes a change.

When leaders consistently show openness and transparency, innovation becomes part of the culture rather than something employees avoid.

3. Give intrapreneurs room to move

Intrapreneurs need autonomy to pursue ideas, but that freedom must exist within clear priorities. A good example from our own work involved a team member who looked at our venture fund website and suggested it needed a major upgrade. The site had been built quickly so we could launch operations, but he believed it no longer reflected the quality of our work. He compared our site with those of other venture funds and showed exactly where improvements were needed.

At that point, we had a choice. We could keep him focused only on his existing responsibilities, or create space for him to improve something important that he had the skill set to do, even if his job description wasn’t related to it. We chose to hear him out and restructure responsibilities so he could develop the new site while continuing his core work.

Startups often benefit when employees can contribute across multiple areas. People frequently wear several hats as organizations grow. The key is balancing experimentation with accountability.

Leaders can support this by creating pilot projects, protecting time for experimentation and setting clear expectations around priorities.

4. Equip them with a founder mindset

One powerful question leaders can ask a team member is simple: What would you do if you were the founder? That question changes perspective. Instead of focusing only on tasks, people begin thinking about outcomes and tradeoffs.

Sometimes this reveals solutions that were hiding in plain sight. Other times, it surfaces obstacles that must be addressed. Either way, it encourages employees to think more like owners. In smaller organizations, this mindset is especially valuable. Teams perform best when everyone feels empowered to contribute ideas about how the company can improve.

Encouraging employees to identify opportunities, evaluate risks and propose solutions helps develop the judgment strong intrapreneurs need.

5. Turn internal wins into competitive advantage

When an intrapreneur proves an idea works, leadership must help scale it without crushing the energy that created it. That usually requires restructuring priorities so the innovator has time and resources to keep building. Leaders should also communicate clearly with the team so everyone understands shifting responsibilities.

An important concept from organizational science is absorptive capacity. This refers to an organization’s ability to recognize new ideas, integrate them into operations and turn them into lasting advantages. Some companies generate ideas stemming from observations outside the organization but fail to absorb them. Bureaucracy or resistance to change prevents innovation from taking hold.

Strong organizations do the opposite. They recognize promising breakthroughs and create the support needed to expand them. The key is avoiding the temptation to over-formalize innovation with layers of approvals and processes that slow progress.

Your next breakthrough might already be inside the company

Many leaders search outside their organizations for the next opportunity. Yet some of the most powerful breakthroughs come from people already on the team. The real leadership challenge is recognizing these innovators early and supporting the ideas they bring forward. Sometimes the next big move is already in the room, whether you’re leading a small startup or a large corporation.

Leaders are often really good at looking out in the world around them to find inspiration for their next breakthrough. They scan the market for pain points, potential customers, partnerships, new products and funding opportunities. But inside large, mature organizations, some of the most powerful innovations often start with a founder’s mindset inside the organization.

Internal innovators, often called intrapreneurs, are closest to the work, the friction and the customer experience. When leaders recognize and empower them, those individuals can drive innovation, speed and competitive advantage that competitors struggle to replicate.

I experienced this early in my career at the Kelley School of Business. A colleague named Brad Wheeler pushed ideas that felt bold at the time. He advocated for a laptop requirement for MBA students and encouraged the use of Lotus Notes to enable digital collaboration among students and faculty. That work became an early version of what we now call a learning management system.

Most entrepreneurs start a business because they want freedom. They envision a Tuesday morning at their child’s school event or a month working from a beachside resort without the constant, low-level anxiety of a standard 9-5. They trade the predictable grind of a corporate job for the promise of autonomy. They convince themselves that being the boss is the ultimate escape.

The challenge is that this reality often ends up being nothing more than a bait-and-switch. Along the way to building the business, the freedom disappears. Instead of creating a business that serves them, they accidentally build a prison filled with huge amounts of responsibility, stress and pressure. Their new “job” ends up demanding more of their time than any corporate boss. Instead of being the captain of the ship, they find themselves in the grimy engine room trying to keep the power on and patch every leak.

Most entrepreneurs assume this chaos is a lack of effort and double down to burn themselves out even further. They believe that once the company reaches success, they will eventually earn the right to be free. Truly free entrepreneurs do the complete opposite. They design the life they want first and then build a business model that is forced to support it.

1. Define your Champagne Moments first

In the startup world, there is an obsession with growth and revenue. While these are critical to the life and health of the business, too much focus on this metric can end up costing you your sanity. What’s the point of achieving $10M in revenue if you haven’t seen your family in six months?

Your Champagne Moments are non-negotiable lifestyle milestones that can set the trajectory for how you build your business. These moments become your North Star to drive your ongoing business decisions.

2. Shift from high-touch to productized delivery

One of the biggest bottlenecks in most companies is the founder’s brain. If your services require your specific expertise to be delivered, you’re operating a high-paid freelance gig instead of a business. This creates a hard growth ceiling and blocks your ability to scale your time.

To reclaim your freedom, you have to productize what you do by turning your expertise into a repeatable system that can be executed autonomously or by anyone else on the team. Freedom starts when you stop being the one doing the work and shift to the one who owns the machine.

3. Hire outcome owners instead of task doers

Entrepreneurs often fall into the trap of “I’ll just do it myself.” This happens because they falsely believe that no one else can meet their standards. If this sounds like you, it could be a sign that you’ve hired doers rather than outcome owners. The last thing you want is to hire people who just wait to be provided a checklist before taking action. This creates an environment where every tiny decision falls on your shoulders.

Instead, true freedom comes from hiring people who are capable of taking responsibility and owning specific results or parts of the delivery process. It’s important to have people on your team who can take expectations and turn them into actions.

4. Reevaluate your high-demand clients

Not all revenue is good revenue. We’ve all had those clients who pay well, but are highly demanding. These types of clients are counterproductive to creating a business that generates true freedom. When clients expect midnight email responses and constant hand-holding, they are a drain on your resources and mental load.

On the other hand, clients who value your standard processes and don’t expect customized solutions require significantly less stress. While firing a high-paying client can be a scary thought for any entrepreneur, it’s sometimes a necessary step toward reclaiming your peace of mind.

5. Monitor your time to value generation ratio

Many entrepreneurs measure their success by the size and value of their company. What they often fail to evaluate is the amount of personal effort required to get there. Making half a million dollars a year looks great on paper, but not so much if the cost is working 100 hours a week.

Instead, focus on tracking and increasing your profit per founder hour. This simple measurement will force you to rethink and remove any low-value tasks that create more strain on your freedom and schedule than they’re worth.

6. Always have an exit strategy

You’ve worked hard to build a successful business. Congrats! The challenge is that you’ve probably been so busy focused on operating the business that you haven’t considered what comes next. Having an exit strategy is important to building a business centered around freedom. This doesn’t mean you intend to actually walk away from the business. However, having a solid exit strategy means that the business no longer needs you. That’s where you find true freedom.

The best way to do this is to make sure that you have a robust set of Standard Operating Procedures (or SOPs). These documented guidelines are a valuable asset to ensure that you can step away from the business at any time and nothing bad will happen.

Moving from an operator to a freedom-focused architect can be a psychologically jarring experience for entrepreneurs. We want to be in control and chase success at every corner. Building a business around your desired lifestyle and freedom will require you to check your ego at the door. It will require trusting a system over your gut instincts or flying by the seat of your pants. But the world doesn’t need more burnt-out founders who sacrifice their lives, family and friends for superficial “success.” Instead of building a business with the hope you’ll eventually gain freedom, start by designing your business around the freedom you want.

Most entrepreneurs start a business because they want freedom. They envision a Tuesday morning at their child’s school event or a month working from a beachside resort without the constant, low-level anxiety of a standard 9-5. They trade the predictable grind of a corporate job for the promise of autonomy. They convince themselves that being the boss is the ultimate escape.

The challenge is that this reality often ends up being nothing more than a bait-and-switch. Along the way to building the business, the freedom disappears. Instead of creating a business that serves them, they accidentally build a prison filled with huge amounts of responsibility, stress and pressure. Their new “job” ends up demanding more of their time than any corporate boss. Instead of being the captain of the ship, they find themselves in the grimy engine room trying to keep the power on and patch every leak.

Most entrepreneurs assume this chaos is a lack of effort and double down to burn themselves out even further. They believe that once the company reaches success, they will eventually earn the right to be free. Truly free entrepreneurs do the complete opposite. They design the life they want first and then build a business model that is forced to support it.

Dave:
When the Great Recession hit, Andy Gill’s business went under. The future he thought he’d created disappeared overnight and the fear of being in that position ever again became his new obsession. So he grinded, he hustled, he faced major setbacks along the way. And in 2022, he got serious about real estate investing. While most people around him upgraded their lifestyles, Andy took extreme measures. He downsized his house, he drove old used cars and he pinched pennies so he could funnel every extra dollar he had toward buying rental properties. Most investors aren’t making these types of sacrifices, but for Andy, it was a temporary trade-off for a more secure financial future and it is already paying off. In just four years, he’s scaled to 58 rental units and counting, and he’s done it all in today’s high interest rate environment without a super high paying job. In many ways, Andy is just the average investor, but he also knows his superpower.
He uses his creativity to cut through the noise, to spot opportunities that fly under most buyers’ radar, and he solves problems for hesitant sellers. Today, he’s even going to pull back the curtain on a genius strategy you’ve probably never heard of, but it’s one that helped him take down a 30 unit property with very little of his own money.
What’s up friends? I’m Dave Meyer, chief investment officer at BiggerPockets. Today in the show we have Andy Gill, an investor in Connecticut who was previously on episode 803 back in August of 2023. And he’s also been one of our most popular speakers at BPCon the last few years. So excited he’s going to be back on the show and hear what he’s been up to. Let’s bring him on. Andy, welcome back to the BiggerPockets Podcast. So good to have you here, man.

Andy:
Thank you. I’m always flattered to be asked and always pinch myself a little bit that I get these opportunities.

Dave:
Well, it’s always great to have you here, Andy. This should be a lot of fun. You have been on the show before, but for people who haven’t heard your previous episodes or didn’t attend your wildly popular session at BP Con last year, tell us just a little bit about yourself, where you are in the country and what you do in real estate.

Andy:
So my name’s Andy Gill. I am on the East Coast in Connecticut, directly between Boston and New York. And we own and operate a portfolio of about 58 apartments currently, all within about 30 minutes of our house. So I’m also a contractor and we’re building new homes, new renovations. I’ve been doing that for basically my whole adult career, so 25 years, but I didn’t start buying real estate. I didn’t understand that owning the asset was the goal until about five years ago. So we’ve been in about four years.

Dave:
Oh, wow. Okay. So you were just doing contractor work for other people, homeowners, real estate investors, I assume, for 20 years. What clicked? What happened that made you realize now is the time for me to start trying to hold onto these assets?

Andy:
I had a really bad business experience that I learned a ton from that taught me that I didn’t understand finance and I didn’t understand a P&L. I didn’t understand any of that. And so I had to get smart. And then I had another opportunity, another mentor and learned how to manage. If you can’t measure it, you can’t manage it. And so being able to project costs and walk it in. And after I kind of developed those skills and people skills, I realized that owning the asset, not just improving it was the path. So we started looking for flips and that didn’t work out. And our first purchase was 12 condos here in Connecticut.

Dave:
So you just went for it.

Andy:
Went for it. I got a partner to go fifty fifty. And yeah, my contracting career, being able to do rinse repeat work, 12 identical condos spoke to me so I could understand. And once I understood one, I understood them all. And regarding the tenants, understanding how rent would move, what the improvements would be, all that stuff, I was comfortable with that. So we jumped in the deep end.

Dave:
What does your portfolio look like now?

Andy:
So we have 58 apartments in various different structures. Amazing. Some we own ourselves, some we own them single partners. And we got into a 12 family with two other partners and they’re all spread. We go as high as Putnam area in Connecticut and low as about Norwich in New London County. And so we manage all of those but 12.

Dave:
That’s a lot. That’s scaling quickly, 58. How did you finance it? Sounds like with partners, but did you have money saved up from contracting?

Andy:
I grew up pretty with limited means and early in my marriage we didn’t have a lot. And my son has cystic fibrosis, which is heavy financial implications. And so it took us a while and I took a real hard hit with that business loss during the Great Recession. So it took a while and we learned to live below our means. And then slowly we realized that we were starting to save. And so we stayed minimal and we drove used cars and we moved to a smaller home and then we had a little bit of cash and we were able to get in with a partner and learned commercial financing. And so that was originally how we went in. We got a commercial loan with a five-year arm and it was a value add. And we created quite a bit of equity in that just by coming in, stabilizing the property.
And then we were able to move some of the equity into other deals. But along the way, once you prove you can do the thing, so if you stay singularly focused on what you’re great at, then people will loan to you. Most of all the financing we do now or most of the loans we get now are private. And so we’ll talk about this deal that we have taken down over the last 18 months and will continue. So like a three-year plan is privately financed.

Dave:
We’re going to turn our attention and talk about this awesome, very cool, unique deal that Andy is doing that I’m very eager to hear about. But I just want to ask you a little bit about that financial sacrifice you made. You said you downgraded, you lived below your means. How did that impact your ability to be a real estate investor? And how do you look back on it now? Was it a big sacrifice? It sounds like it was worth it, right?

Andy:
Yes, it certainly was worth it. At the time, I think it was more out of fear at the time. I was afraid of debt. And now debt being good versus bad and how you define that is different for everyone, but I really just wanted to… I didn’t want to owe anyone anything. And so living below our means was freedom for us. So I didn’t want to have to work to pay for a car that other people viewed as us being well off.That didn’t mean anything to me. Good. So we downsized the house and I raised my two kids in an 800 square foot house. It was still 850 square foot house. And we’re still here now. And so was it a sacrifice? I mean, I guess, but it was how I felt safe at that time. And then I realized that we were growing a net worth with equity and savings.
And then when it was appropriate, then we shifted that into investments. So yeah, I think that living below your means, I think understanding what your overhead is and everyone should look at their personal as overhead and being able to clear that. And I don’t mean everyone, not everyone has the ability to do that, but if you do have the ability to live below your means, you should.

Dave:
You mentor a lot of people, right? You talk to a lot of real estate investors. Do you find a lot of people are willing to do this to sort of reduce their lifestyle even if it’s just temporary to pursue real estate?

Andy:
I don’t think everyone sees the value from a social media high level, okay, this is the life. You buy these things, people pay rent and you make money, lots of money, but it’s not passive. So when you start talking about what it actually takes and the amount of grind and the different steps, so to get through acquisition is a marathon. And then you start and then you meet your tenants and then you have to figure out how to screen tenants and collect rent and do maintenance and what value add you should do and how do you do all this stuff. So there’s a ton of education with it, but a lot of people do not follow through or they don’t see the value in it. I think you really have to want it. And I think that you have to dig in and put some of your wants and desires in the parking lot for later.

Dave:
Yeah. I think that is true. It can become passive, but it can’t be passive upfront. If that’s what you want, you either have to be already really rich and so you can go and be a lender or go invest in syndications or something, or you should just invest in the stock market. It’s very difficult to say, I simultaneously want an avenue, a path to accelerate my financial situation that’s better than every other option out there, like real estate, I believe it is, but I also don’t want to do anything.That is a really hard thing to ask for unless you are fortunate and are already really wealthy. And I just think not everyone has to downsize their house or drive a used car, but you got to find something that you’re willing to give up to pursue it. It’s not free. You have to put something into it.
And I’ve found a lot of younger people are willing to do what you’re talking about. When I started, I was 22. I lived in my friend’s grandma’s basement for three years. I didn’t even think twice about it. It was fine. I was like, “Yeah, whatever. It’s a bed.”
But I do think doing it at the age you’re at when you had kids is something that I hear of less. How long ago was that?

Andy:
We’re in our fifth year now. Fifth year. Yeah. Yeah. We started, I’ll be 49 this year, so I was 44 when we bought our… I mean, we’d done flips earlier. I’d been a contractor a long time, but the first buy and hold, I was 44.

Dave:
Wow. And so five years later, I would assume with what you’re telling me, financial situation trajectories completely changed by making those sacrifices about your lifestyle, but also putting in a lot of work and just sticking with it.

Andy:
Yeah. I didn’t have a 401k. We were just paying for trying to pay mortgage, keep food on the table. And so I knew I had to do something. And so we went for it. I didn’t know I was going to get in when it was still going up. Interest rates were already spiking and I didn’t think it was going to be like this, but I had a belief in myself. I got good at something and I identified the specific metrics that I needed to monitor and watch and it’s gone well. And now when we buy things, we have a good plan and we go to execute it, but if it doesn’t go as well, we know when to let it go.

Dave:
Well, awesome. Good for you, man. I love hearing your story. It’s super inspiring and relatable. It’s something that really everyone can do and just happy for you and all the success you’ve had. Thank

Andy:
You, man. But

Dave:
You haven’t stopped, obviously. And you told me you’re doing a really cool, interesting deal that’s going to really expand your portfolio. And I want to dig into that, but we got to take a quick break. We’ll be right back. Welcome back to the BiggerPockets Podcast. I’m here with investor Andy Gill. Before the break, we talked a little bit about Andy’s background and how he got to where he is today with a sizable portfolio in Connecticut. But Andy, last time you were on the show, you said, I think you told us that you were ready to do something new, but you didn’t know exactly what it was going to be. Now you know what it is, right? So tell us about it.

Andy:
Yeah. So I had an idea. I figured that if I could take under management of properties that I didn’t yet own in older landlords that I knew would be selling that were a bit frustrated, I’d be already controlling the property and be able to be in the first position to make an offer and acquire that property. So I sent out a bunch of mailers that I designed with AI and they were really cool. And it basically said, “Being a landlord sucks, you should sell to me. ” Something along those lines. I don’t remember. It was like cartoons and stuff. And I hit one of my longtime friends and builders that I didn’t know owned properties or I forgot that owned a bunch of apartments. So we talked and I was like, well, he’s like, “My wife is all over me. She wants me to sell.
She wants to travel more, blah, blah, blah.” And I’ve been working with this guy for 20 years. Fast-forward a year and then he’s like, “I think I’m ready to start talking to you about that. ” And so we kind of curated this deal where he didn’t want to pay the capital gains and he wanted to be careful about the depreciation of capture, but he bought a long time ago, so it was pretty minimal. And so I created a proposal where we would transfer properties to me staged over time and he would hold a note and we’d put a small amount down. But I wanted to manage them upfront right away so I could see under the hood and get comfortable just because we had limited capital to take on something this big without partners. So we started doing that and it took a while, took a year to put all together and it was a phased acquisition where we bought some, managed others, and then over time transferred the rest of those into our ownership, into our portfolio.
So we’re about halfway through that now and plans of transferring the remainder in the coming 12 months, I guess.

Dave:
This very cool. All right. We got to talk about this and dig into this. So first and foremost, your thought was if I basically become a property manager for other landlords, I assume you can make some money in it, but you weren’t really doing it for that. You were doing it for deal flow. As those landlords potentially want to sell and offload, they’re going to come to you first and you’ll have early access. I love that strategy. Did someone tell you to do that or did you just think of that on your own?

Andy:
No, that was me. That was my thought process.

Dave:
Wow, it’s genius.

Andy:
Thank you. Yeah. Don’t tell anyone about it, all right?

Dave:
Yes.

Andy:
Tens

Dave:
Of thousands of people are about to hear that idea and copy you.

Andy:
It is. I mean, but it really comes down to would these people hold financing for others? Well, you need to develop the skills so that they would. And so yes, they will if you prove yourself, if you add value. So I take care of problems and I let that be known. And it has become more safe to transfer it to me than anything else as time has gone on.

Dave:
I love that strategy. It makes so much sense. So tell me about the mailers because a lot of people send mailers. I as a landlord get all of them all the time from wholesalers, from people who want to buy my properties. What were you saying that was different than just a normal mailer that goes out?

Andy:
You want to be relatable and approachable in the real world as well as in the perceived world. So I designed a cartoon character of myself and what I do. So I use all the images of… I wear flannels. I’m a very tactile hands-on person. I do my own lawn mowing and snow removal as much as I can. I have to hire a lot of it out, but I’m very hands-on. So I wanted to relay that in who I am and what I do. And it worked. It was like a flannel and a tool belt and a dog and a pickup truck. And it basically said, I’m a landlord too. It sucks. It sucks. You’re probably done anymore.

Dave:
I get it.

Andy:
Yeah. People call you and it must be annoying. Must suck. You should sell to me. So something like –

Dave:
Do you actually think being a landlord sucks?

Andy:
No, I love it. I actually

Dave:
Love it. I don’t either. I don’t think it sucks. All these things are like, “Oh, be a landlord sticks, do passive.” I’m like, “Really?” There are annoying parts, but there’s annoying part of every job. No, I know. I love it. Yeah. Okay. But you’re selling it, so I get it. And especially too, if you’re hitting someone who’s been a landlord for 30 years, maybe they’re over it. And that I could see. And you’re fresh, man. You’re five years in. So yeah, you’re ready to go. I got fresh legs. Yeah.

Andy:
Yeah. Yeah. 49-year-old fresh legs, but yeah.

Dave:
Super fresh. Yeah.

Andy:
And it worked. I got a bunch of calls. I actually got a bunch of calls on that one mailer. I think we sent out like 600 mailers or something like that. And I got 100 calls about it. Wow.

Dave:
What? That’s very cool. I just want to say too, because you’re a big AI user and we’re going to talk about that in a little bit. But I just like that you used AI to be unique in an individual. Because I think if you just go on and use AI and use the template, like you said, that anyone else uses, you’re not standing out. It’s no different than just hiring another company to do it, but you sat down and though about, who am I? How can I showcase myself? And then you use AI to do the execution. That to me, I assume you attribute the success of that mailing campaign and the response rate you got to just by doing something a little bit different.

Andy:
I did a follow-up to that too with a handwritten squasi handwritten letter and it said being a landlord stinks. And I got scratch and sniff snickers of dead fish. And I put them in…

Dave:
It’s the most New England thing I’ve ever heard.

Andy:
Yeah, I did. I bought them on Amazon. It was like scratch and sniff stickers. Yeah.

Dave:
Okay. All right. So anyway, your friend, this guy you know, he calls you. How big is his portfolio? 30

Andy:
Units. 30 units. Nice. It’s a mixed spread. Yeah, it’s spread out over seven properties.

Dave:
Okay. And close in your target area. He’s been doing this for a while, it sounds like his wife wants to travel, but he doesn’t want to sell it today, right? And it sounds like you didn’t want to buy it today.

Andy:
I mean, I would’ve had to bring in partners so I didn’t have the cash to take this whole down all at once without giving up significant equity, which would’ve been fine too, but he didn’t want that.

Dave:
And so what’s the structure? Let’s walk through it. You figured out a way you take over management, that was the first step?

Andy:
Yep. So it was two contracts. So the first would be the management contract for duration of time. The second contract would be for the purchase and sales. Yeah.

Dave:
Did you agree on prices for the sale upfront or was it just kind of like a right of first refusal where if he decided to go sell, you had the first shot at buying it and making

Andy:
It off? Yeah. So the first one we did the appraisals and it went based on that. The remaining ones were with prices to be agreed upon at current market. We actually just agreed on a per unit price because we’re like, “Let’s stop paying for apraisals.” So

Dave:
You just basically said, “You have 30 units, I’m going to pay you. I’m going to make up a number, $100,000 a unit and we’re not going to go and get eight appraisals right now.”

Andy:
Right. Because then you’re like, “It’s fine. You win some, you lose some, but some are three bed, some are two beds, some are in better areas than others. But if you’re taking the whole thing, it made sense.

Dave:
Well, I imagine a big part of the appeal of this to the seller is simplicity. He doesn’t want to spend half of his days right now with appraisers and title agencies and make it simple. And so how far are you into this deal structure?

Andy:
We’re about halfway. Yeah.

Dave:
So you’ve been managing the properties for how long?

Andy:
Coming up on a year now. Managing the property. Yep. It’ll be a year soon and we’ve transferred three of the seven properties

Dave:
And

Andy:
We’re working towards the remainder. Yeah.

Dave:
Awesome. That is so cool. And how are you feeling about the structure? Is it working well for you?

Andy:
It works really well in that for management, it works really well because I’m already in control of the property completely. I already know the tenants. I already know what the problems are. So good. I’m already collecting rent. So essentially I basically just go into rent ready and move it from his account to mine.

Dave:
And do you think the seller’s happy with the arrangement too?

Andy:
Oh, he loves it. He loves it.

Dave:
Yeah.

Andy:
So he’s a builder also. And so now we’re talking about going into development because as he wants to retire, he wants to stay involved and doesn’t actually want to retire. He wants to work less. So we’re talking about developing other rental properties. There’s a thing called an 830G here, affordable housing. And so he’s getting into that developments where we can essentially disregard the zoning regulations and increase density. So he’s into that. So we’re working on some developments that we would partner on also. So we get along really, really well. He’s an awesome guy.

Dave:
That’s so great. Did you follow up with other investors who responded to your mailer? Or once you found this, was that sufficient?

Andy:
I did. There were some in, but they all were just like every other that you get a call from a postcard. So some of them, hey, maybe later, whatever. And so I was keeping a spreadsheet, but then once we got into this, I was like, this is all I can… I’ve bitten more than I can chew right now, so we need to stagger this. I basically stopped. I don’t chase down any deals. I get phone calls on them a lot. Yeah. Oh, good for you. Stuff that if you singularly focus on being good at something, you will get referrals and things will come your way as you develop and grow.

Dave:
That is such good advice and so true. You don’t have to be good at everything in real estate, but if you can be good at one thing and people can count on you for that one thing, it’s going to help your career. Well, congrats, Andy. It’s super cool. I love the approach that you’re taking here. Something I would try to emulate. Maybe not doing the property management, but buying a portfolio. I love the idea. And as you said, Andy is good at this. You mentioned that you manage your properties with RentReady. If you are a BiggerPockets Pro member, you can get a discount on RentReady. It’s an incredible deal. It basically pays for the BiggerPockets Pro membership. If you want to check that out, go to biggerpockets.com/perks. All right, Andy, I want to turn more towards just some advice because I know you mentor a lot of people and help a lot of people with real estate.
I want to hear the advice that you’re giving people to navigate the unique market that we’re in right now. But we got to take one quick break. We’ll be right back. Welcome back to the BiggerPockets Podcast. I am here with investor Andy Gill. We’ve heard a little bit about his background and story and about the very cool, unique deal structure you came up with to really supercharge your portfolio building. You mentioned, and you and I have talked about this, but you help a lot of people build their real estate investing careers. What are some of the things you’re seeing people struggle with? And maybe what’s some of the advice that you’re giving to help people move forward with financial freedom through real estate?

Andy:
The advice I’m giving currently is to be persistent. You have to make a lot of offers. My son is actively trying to buy his first property. Oh, nice.He moved into one of his… He’s 20 years old. He’s got pre-approved for an FHA loan. He’s doing great. And when I watched him make his first offer, you’re emotionally tied to it. So he wanted to get that deal because we picked it apart and it’s not going to be that deal. It’s probably not going to be that deal. It’s probably going to be the 15th or the 20th or the 30th deal that you… And so kind of scan them at a higher level and be persistent and make lower offers. Underwrite without the price in mind with what works for you for cashflow.

Dave:
It’s just about sticking with it right now.

Andy:
It’s

Dave:
Just good. I saw Michael Zuber from One Rental at a time, his community. He was saying that this is the era for low ballers. I like that. And it’s not like you’re necessarily trying to screw people over, but you’re just showing them what you’re willing to pay. And someone will agree to that. At some point the sides will align and there will be mutual benefit, but it’s not going to be everyone. So you just really need to be patient with it. Do you find that’s hard for new investors to accept?

Andy:
Yes, I do. So it’s two part. Be persistent, but also believe in your own abilities to figure things out. So your first deal doesn’t have to be a home run. It just has to get you on base. So if I know that when I get into a deal, if you miscalculate something, if some conditions are discovered afterwards, you’re going to fight through it. And you have to be able to believe in your abilities to get yourself out of jams. So don’t hide behind like, “Oh, well, I need to have X amount of cash flow in order to do this. ” Figure out what would you pay? What would you buy it for? And then find the mean of that and just do it. Get on, get enough, get around people that will validate that, get in the right rooms and then go for it, create a network and swing the bat.

Dave:
That makes sense to me. You said cashflow. Are there any other minimum thresholds that you feel a deal needs to hit these days?

Andy:
For these multifamilies that we’re buying, we have cashflow. We’re already looking for… I mean, cash on cash is… I want to get my money back as fast as possible. I also want to be able to… I want to buy in a place that gets 3% organic appreciation historically. I’m not looking for a place that’s going to just parking money, but that’s not going to grow.

Dave:
I know, but that’s not asking. 3% is pretty normal. So you’re not saying I need to be in Austin in 2020. Yeah, it’s just, I

Andy:
Get it. But when there’s no deals, the deals that are available are typically in the area that you can buy areas that sit flat. Yeah,

Dave:
That’s fair.

Andy:
So stay out of that.

Dave:
And then what about condition of property? Because New England, there’s a lot of old stuff around there. So are there any things you won’t touch or what kind of properties do you look for?

Andy:
It’s funny you say this because the things that are acceptable to me and the things that I see other investors being like, “Oh, I’m afraid of that. ” I mean, I don’t like knob and tube wiring. I want to do that. I like to get a good roof on the place. I want to know structural problems. We have a lot of stone foundations here. I mean, you get out in our basements in New England and you’re like, “Someone was killed here for sure.” Then like, oh, there’s weird stuff. So there’s limited amount of things. I mean, if you look at bad roof structural problems, et cetera, knob and tube wiring, things that cost a ton of money to… I also like sewer laterals. We have old infrastructure here. So there’s your electrical service, your sewer and water. You want to make sure you get that inspected all the way out to the street.
That’s a very, very expensive find later. So there’s a short list of things that I say, stay away from this, stay away from that, or at least get it resolved when you’re in contract.

Dave:
Okay. But would you give that advice for people who might not have your background in construction and contracting? Do you think for people who don’t have that background, you would change the criteria of what to buy?

Andy:
No, I wouldn’t. I mean, like you said, we started this. This is not passive income. If you’re going to come in, you’re going to have to work. And so you’re going to get calls on Saturdays and Sundays and there’s problems that are going to happen. Someone else is not going to come in and buy something better than me at a price better than I can buy and not have the problems that I have. So you’re going to have to figure it out. You’re going to have to go through the renovations, you’re going to have to go through the heavier CapEx problems. You’re going to have to figure it out if you want to be in this game.

Dave:
It’s good advice, man. I like that. Figure it out. You can. That’s being an entrepreneur. You don’t know what’s going to happen, but you can figure it out. You

Andy:
Absolutely

Dave:
Can. Thousands of people have done it. That’s literally the whole point of BiggerPockets too. You run into a problem you can’t solve, go on the BiggerPockets forums, ask a question. Someone will help you. Come to BPCon and you can meet people who can help you. That’s the whole value of having a network. I mean, look at Andy. Having a network landed him this sweet deal with 30… It’s just like you can absolutely do this. Speaking of BPCon, Andy, you had a wildly popular session on using AI with real estate last year. And I understand you’re coming back this year and doing more on AI.

Andy:
Yeah.

Dave:
I think it’s super fascinating because I’ll be honest, I use AI a decent amount, not that much for real estate investing. So tell me what you’re talking about at BPCon and what investors might learn.

Andy:
Well, last year I documented how I use AI, so the different frameworks and how I use it. It was an incredible opportunity. I’m incredibly grateful for it. I never thought I’d speak on a stage with so many people. There was

Dave:
Like 800 people there.

Andy:
Yeah. It was crazy.

Dave:
Andy went viral at the conference basically.

Andy:
Thank you. Yeah, it was pretty cool. It was an experience I’ll always remember. And so this year I was asked to host a AI focused networking session. So the networking sessions at BP Conner, if you haven’t gone to BPCon, it’s absolutely incredible. This will be my third year speaking, I think my fifth show and I won’t miss it. I love the networking stuff and I like how every year it gets more focused on networking. So I’m going to be doing a 20-minute talk on AI and how I use it, but this time focused on other people talking to other people about how they use it. I want it to be of value in the last two years. I really spend quite a bit of time making sure that I want it to be digested really well and people don’t walk away with being like, wow, that was incredible value.
And I beat the hell out of myself to get there. I was super late last year in submitting it. I’m like, “It’s not ready. It’s not ready.”

Dave:
I do the same thing. I’ve always It’s like tinkering till the last

Andy:
Day

Dave:
Of my speech. But yeah, it was super popular, one of the highest rated sessions that we’ve ever had. And yeah, I love the idea that you’re obviously sharing what you do, but AI is so new. It’s interesting always to hear what other people are doing with it. No one has the one right answer right now
And people are super creative about it and I’m super excited to come to this and hear how other people are using it because even just in regular life, I sometimes hear how people are using AI to automate tasks or things they do in their day. I’m like, I never would’ve thought of that. So that will be a lot of fun. If you want to grab your ticket, go to biggerpockets.com/conference. Join me and Andy, Henry and thousands of other investors learning and sharing with one another. As Andy said, it’s a can’t miss event. I look forward to it every year. Super excited for this one in Orlando, October 2nd to 4th. Well, Andy, thanks for joining us again, man. Always enjoy talking to you, learning from you. Congrats on all your success, cool deals that you’re up to. We really appreciate your time.

Andy:
Thanks, Dave. I appreciate it. Thanks for having me.

Dave:
If people want to connect with you outside of BPCon, where can they do that?

Andy:
I am primarily on Instagram. I’m not on the other platforms. Coach Andy Gill, G-I-L A – N-D-Y-G-I-L. And I try to answer all my DMs and I’m an idiot on there and post all kinds of surgery things.

Dave:
No, I like your content. It’s fun. Well, check him out there, Andy, there on Instagram and at BPCon. That’s our show for today. Thank you all so much for watching this episode of the BiggerPockets podcast. We’ll see you all next time.