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When founders ask me how to start with SEO, they usually expect a tool recommendation. The honest answer is that the tool isn’t the problem. The sequence is.

For the past few years, my agency has been refining the same end-to-end SEO process — the one I now use with every new client and break down across an eight-module curriculum we run for our team. The steps work because they’re ordered. Most founders fail at SEO not because they skip steps but because they do them in the wrong order: writing content before researching keywords, building links before fixing crawl errors and chasing traffic before defining what kind of traffic moves their business.

Here’s the 10-step sequence I follow, in the order I follow it. You can run all of it yourself for the cost of two free tools and a few weekends.

1. Start with niche research, not keyword research

Before you type a single seed keyword, define what your business actually has the right to win on. A skincare brand selling to dermatologists shouldn’t try to rank for best moisturizer. A SaaS for restaurant owners shouldn’t compete on small business software.

Write down the three or four sub-categories your business owns. Sanity-check each one against the competition in Google’s results. If the first page is dominated by Wikipedia, government sites and major publications, narrow further. Niche before keywords. Always.

Take 30 minutes and write down every phrase your customers actually use to describe their problem, in their own words. Look at your inbound emails, sales call transcripts and product reviews. The vocabulary your customers use rarely matches the vocabulary you use internally — and the customer vocabulary is what ranks.

Once you have a list of 30 to 50 seed terms, open Ahrefs or Google’s Keyword Planner. Tools are for expanding what you already know; they’re terrible at telling you what to know in the first place.

3. Layer in the specialty keyword types your competitors miss

There are at least nine specialty keyword formats most agencies ignore: geographic, seasonal, event-based, question-format, service-based, commercial, comparison, best-of and alternative-to. Each one maps to a different stage of the buying journey, and each one is usually less competitive than the obvious head terms.

In a recent niche project, layering comparison and alternative-to keywords on top of a head-keyword strategy roughly tripled the addressable search volume — without touching a single competitive primary term. The same pattern shows up in nearly every site I audit.

4. Tag every keyword by search intent before writing a word

Every keyword falls into one of four intent buckets: informational, navigational, transactional or commercial investigation. The same phrase can mean different things to different searchers, and the only way to know is to look at what’s currently ranking on page one. Google’s own guidance on understanding user intent comes down to the same principle: match your page to what the searcher actually wants.

If page one is full of blog posts, the intent is informational. If it’s full of product pages, the intent is transactional. Match your page type to the intent before you decide what to write. Mismatched intent is the single most common reason good content fails to rank.

5. Fix your technical foundation before publishing anything new

Before adding new pages, run your site through a free Screaming Frog crawl and Google’s PageSpeed Insights. Look for four things: crawl errors, broken internal links, slow Largest Contentful Paint on mobile and any redirect chains longer than one hop. Each one is silently capping the ceiling on every page you publish.

This is unglamorous work. It’s also the work that determines whether the next six months of effort compound or evaporate.

6. Standardize your on-page template across every new piece

Decide once, then never re-decide: how your title tags are written, how your H1 relates to your title tag, where your primary keyword appears, how internal links are formatted and what your URL structure looks like.

I keep a one-page template that goes on every content brief we send writers. It saves hours of editing per article and produces consistent results across writers who have never spoken to each other. Standardization is what lets you scale; ad-hoc decisions are what burn content teams out.

7. Build content in clusters, not in isolation

For every commercial keyword you target, plan a cluster: one pillar piece and three to five supporting pieces that link inward to it. Search engines reward sites that demonstrate topical depth, and clusters are the cleanest way to demonstrate it.

A single well-built cluster of six pages around one commercial topic will outperform 30 disconnected blog posts every time. Test that against your own analytics if you doubt it. The math is one-sided.

8. Earn links through original data, not cold outreach

Cold outreach link building has been the lowest-yield activity in SEO for at least three years. The replacement is original research: publish one piece per quarter that contains data nobody else has — even if your sample size is small. Journalists and bloggers cite primary sources because primary sources make their work easier.

Last year, one of our small-sample data pieces earned more high-authority backlinks in two months than a previous client’s six-month outreach campaign. The ratio wasn’t close.

9. Track three metrics monthly — and ignore the rest

The SEO industry has trained founders to obsess over dashboards. The truth is that three numbers tell you almost everything: how many of your targeted commercial keywords are ranking in positions 1 to 10, how much qualified organic traffic those rankings produce and how many of those visits assist a conversion.

Ranked positions tell you if your work is paying off. Traffic tells you if the rankings are valuable. Assisted conversions tell you if the traffic is worth the next month of investment. Everything else is noise until you’re operating at meaningful scale.

10. Audit, dedupe and prune every quarter

Most sites lose more SEO performance to keyword cannibalization, duplicate intent and stale content than they gain from new publishing. Every 90 days, audit your existing content: which pages are competing against each other for the same query, which are pulling impressions but no clicks and which are pulling neither?

Merge the cannibalizing pages. Refresh the impression-rich but click-poor pages with better titles and meta descriptions. Redirect the truly dead ones to their nearest healthy cousin. Pruning is unglamorous work that often produces the single biggest one-quarter SEO lift any site will ever see.

The system above isn’t proprietary. Every step is something a careful agency would do, in roughly the same order. What separates the founders who win at SEO from the ones who plateau isn’t access to a secret framework. It’s the discipline to do all 10 steps in sequence, on a quarterly cadence, for two to three years before judging the results.

By the time you do hire an agency, you’ll know exactly what to ask. The ones that can’t answer those questions will filter themselves out before they bill you.

When founders ask me how to start with SEO, they usually expect a tool recommendation. The honest answer is that the tool isn’t the problem. The sequence is.

For the past few years, my agency has been refining the same end-to-end SEO process — the one I now use with every new client and break down across an eight-module curriculum we run for our team. The steps work because they’re ordered. Most founders fail at SEO not because they skip steps but because they do them in the wrong order: writing content before researching keywords, building links before fixing crawl errors and chasing traffic before defining what kind of traffic moves their business.

Here’s the 10-step sequence I follow, in the order I follow it. You can run all of it yourself for the cost of two free tools and a few weekends.

The four moves any non-coder can use to launch a one-person business this week.

Key Takeaways:

• Discover what “vibe coding” really means — and why 63% of the people using it to build real businesses have never written a line of code.
• Watch how one solo founder built a $401 million business in year one with $20K and his brother as his only employee.
• Screenshot the exact Perplexity Computer prompts that reverse-engineer what four solo founders did to build their businesses — without figuring it out from scratch.

You have the idea. You have the laptop. You have every AI tool on the market open in a tab. And you are still not launching anything.

That is the quiet frustration behind the biggest shift in one-person business formation of the last decade. The tools are here. Most solopreneurs are still waiting to feel technical enough to start. The founders in the video above stopped waiting — and the moves they made are not what most solopreneurs expect.

The four moves I break down in the video above are designed to fix that — starting with the one most non-coders skip.

“Vibe coding” is the term Andrej Karpathy, one of the co-founders of OpenAI, coined in early 2025 to describe a new way of building software. You describe what you want in plain English, an AI writes the code, and you refine it by conversation instead of syntax. It sounded like a joke a year ago. According to Startup Fortune, it is now a $4.7 billion market growing at 38% a year, with 63% of active users identifying as non-developers.

This is not a fringe movement. Axios reported in June that Americans are starting one-person businesses 20% faster than they were a year ago, while startups planning to hire employees have stayed flat — a shift Nasdaq’s economists tie to autonomous coding tools. Intuit’s 2026 AI Impact Report, built on more than 34,000 SMB owners, found that 43% of AI-using businesses say AI has increased their revenue, versus just 2% who say it has gone the other way.

That compression is what Rule 5 of my book, The Wolf Is at the Door, is really about. In a world where the software builds itself, adaptability is no longer about learning faster than the market — it is about shortening the loop between what you see and what you launch. The reason a solo founder can now sell a company for $401 million with almost no employees is not that AI made him smart. It is that AI has collapsed the reaction time that used to give bigger competitors the advantage. That opportunity is now in your hands, no seven-figure marketing budget required.

This weeks video breaks down how Matthew Gallagher launched Medvi in two months with $20K and his brother as his only employee, how Billy Howell charges $750 to $2,500 per app with no coding background, how the creator behind BridgeMind made $42,630 in 142 days building live on YouTube, and how KEV hit $100,000+ in revenue and 67,000 users across four apps — plus the four Perplexity Computer prompts to reverse-engineer their moves in your own business this week.

Every founder, every move and every prompt is walked through in the video above — including the four Perplexity Computer prompts that turn what took these founders months of trial and error into a single afternoon of work.

The free AI Success Kit, available to download for a limited time, comes with a free chapter from my new book, The Wolf is at The Door – How to Survive and Thrive in an AI-Driven World.

The four moves any non-coder can use to launch a one-person business this week.

Key Takeaways:

• Discover what “vibe coding” really means — and why 63% of the people using it to build real businesses have never written a line of code.
• Watch how one solo founder built a $401 million business in year one with $20K and his brother as his only employee.
• Screenshot the exact Perplexity Computer prompts that reverse-engineer what four solo founders did to build their businesses — without figuring it out from scratch.

You have the idea. You have the laptop. You have every AI tool on the market open in a tab. And you are still not launching anything.

Bijo Thomas was expecting a human being to interview him for a job as a senior AI solutions architect role at talent acquisition brand Experis. When he opened up his laptop for an interview, he instead came face-to-face with an AI avatar named Sophie. 

Thomas recently told Business Insider about the experience. He said that Sophie looked like a human being from the neck up, and she smiled and asked follow-up questions throughout the interview. 

“It was very realistic,” Thomas told BI. He passed the interview and went through two more rounds, each time with human interviewers. He got the job and joined in May.  

Thomas’s experience reflects a growing trend. AI is moving beyond sorting through large piles of resumes and extending its reach to early-stage job interviews. Companies like cryptocurrency platform Coinbase and automation software company Zapier have quietly begun using AI to screen candidates in interviews, BI reported. 

Industries like retail and manufacturing first used AI in job interviews to meet high-volume hiring targets. Now the practice is gaining steam for weeding out candidates seeking full-time, white-collar positions. 

Employers are reluctant to publicize their dependence on AI 

Employers aren’t touting the use of AI systems in hiring, partly because of debate around AI. According to BI, it remains to be seen whether AI chatbots have a positive impact by reducing human bias in hiring or a negative effect by alienating candidates. 

“The interview process is arguably the most human part of recruiting,” Kyle Lagunas, an HR tech industry analyst, told BI. He added that employers could be concerned about how it would look to candidates to outsource this human element of recruiting to AI. 

At some companies, however, applicants must pass through AI interviews before they can make an impression on human interviewers — and at times, the AI gatekeepers are necessary due to the sheer volume of job applicants. For example, Coinbase faces a flood of applications, about 1.5 million per year, L.J. Brock, the platform’s chief people officer, told BI. 

“No matter how big my recruiting team is, no matter how hard we try, we can’t get to 1.5 million people,” he told the outlet. 

Coinbase turned to AI to manage interviews starting in August. The company introduced an AI interviewer named Milo to handle interviews for roles below the director level. Since Milo’s release, Coinbase has brought on more than 240 new hires initially filtered by the AI. 

Another company finds ‘hidden gems’ with AI interviews

Coinbase isn’t the only company to experiment with AI interviews. Zapier also rolled out AI interviews last year after realizing that its job postings immediately drew thousands of applicants — far more than it was possible for humans to screen on their own.

Tracy St.Dic, Zapier’s global head of talent, told BI that AI interviews have allowed the company to screen up to five times more applicants than normal and allowed candidates to advance through the hiring process on the basis of more than just their application and resume. St.Dic called these applicants “hidden gems.”

Bijo Thomas was expecting a human being to interview him for a job as a senior AI solutions architect role at talent acquisition brand Experis. When he opened up his laptop for an interview, he instead came face-to-face with an AI avatar named Sophie. 

Thomas recently told Business Insider about the experience. He said that Sophie looked like a human being from the neck up, and she smiled and asked follow-up questions throughout the interview. 

“It was very realistic,” Thomas told BI. He passed the interview and went through two more rounds, each time with human interviewers. He got the job and joined in May.  

For some young people in the U.S., higher education is losing its luster.

New college graduates are currently facing the worst entry-level job market since the pandemic, per The Guardian. 

What’s more, the average tuition for both public and private four-year colleges has essentially doubled over the past 30 years when adjusted for inflation, NPR reported last year. 

Undergraduate enrollment was 15% lower in fall 2021 than in fall 2010, with 42% of the dropoff taking place amid the pandemic, according to the National Center for Education Statistics.

High school graduates who plan to join the workforce right away might wonder which no-degree-required roles pay the most.

Online lender NetCredit’s new study, which examined occupations that don’t require a degree (per the BLS Occupational Handbook) and the average yearly salary for each role, reveals the highest-paying job options in the U.S. 

The top seven no-degree roles boast national average salaries ranging from $102,482 (gambling managers) to $122,824 (nuclear power reactor operators). 

Transportation, storage and distribution managers, with an average wage of $116,022, and police sergeants and captains, with an average wage of $110,989, rounded out the top three best-paying occupations that don’t require a college degree. 

Read on to see all of NetCredit’s no-degree, six-figure jobs, along with 18 others that offer national average wages starting at about $85,000:

For some young people in the U.S., higher education is losing its luster.

New college graduates are currently facing the worst entry-level job market since the pandemic, per The Guardian. 

What’s more, the average tuition for both public and private four-year colleges has essentially doubled over the past 30 years when adjusted for inflation, NPR reported last year. 

Undergraduate enrollment was 15% lower in fall 2021 than in fall 2010, with 42% of the dropoff taking place amid the pandemic, according to the National Center for Education Statistics.

High school graduates who plan to join the workforce right away might wonder which no-degree-required roles pay the most.

Online lender NetCredit’s new study, which examined occupations that don’t require a degree (per the BLS Occupational Handbook) and the average yearly salary for each role, reveals the highest-paying job options in the U.S. 

The top seven no-degree roles boast national average salaries ranging from $102,482 (gambling managers) to $122,824 (nuclear power reactor operators). 

Transportation, storage and distribution managers, with an average wage of $116,022, and police sergeants and captains, with an average wage of $110,989, rounded out the top three best-paying occupations that don’t require a college degree. 

Read on to see all of NetCredit’s no-degree, six-figure jobs, along with 18 others that offer national average wages starting at about $85,000:

Terry Kurth, 77, says that choosing the right life partner is the most important decision an individual can make — and he knows the truth of this statement firsthand. Nearly 50 years ago, his wife was in labor. She was in the hospital lying on her side with severe back pain because their daughter, Amanda, was turned 180 degrees in the womb.

Terry was there for his wife — but he also didn’t stop working. 

“I had one hand on the small of her back to relieve pain and the other on the phone calling prospects to sell lawn care,” Terry tells Entrepreneur in a new interview. “She didn’t complain because she knew we were about to have another mouth to feed, and failure wasn’t an option.”

Terry entered the Weed Man system in 2000 after exiting his own lawn care ventures and searching for his next chapter. He quickly saw an opportunity to expand the Canadian brand in the U.S. and founded Epic3, which would become Weed Man’s largest multi-unit ownership group. Starting with a single territory in Madison, Wisconsin, Terry steadily scaled the operation into a nationwide footprint.

Andy Kurth’s entry into the business was far less strategic. As Terry’s son, he joined while in college simply to earn extra cash, working in sales and as a lawn care technician. But what began as a temporary gig evolved into a long-term career. Over time, Andy took on increasing responsibility, eventually rising to become president and CEO of Epic3 and leading the continued expansion of the business his father helped build.

The following interview with Terry and Andy has been lightly edited for clarity and concision.

Early days

How did you end up in lawn care and franchising?
Terry: I was going to be an engineer and went to the University of Wisconsin, graduating in 1975. While I was there, I started working at a golf course and fell in love with being outside and working with turf.

I ended up getting a degree in agronomy, which is essentially plant science, and became a golf course superintendent right out of college. Later, I went to work for the Scotts Company in its professional turf division and traveled around the country giving educational seminars to golf course superintendents, landscape contractors and early lawn care operators.

Eventually, I came into contact with a company called Barefoot Grass, became one of its first franchisees in 1978, built that up and ultimately sold when Barefoot Grass was acquired by TruGreen. It ended well, and I found myself gainfully unemployed in my mid‑40s with the proceeds from that sale.

What did you do after exiting Barefoot Grass?
Terry: After Barefoot Grass was sold and I completed that chapter, I became past president of what was then the Professional Lawn Care Association of America (PLCAA), which gave me a strong network of operators across the country. Weed Man is headquartered in Toronto, and through that network, I got to know their leadership. They flew me up; I met the franchisor and a Canadian franchisee who had acquired the master rights to the United States, and together we came up with the idea of creating regional sub‑franchisors. My region included Minnesota, Wisconsin, Illinois, North Dakota and South Dakota. I sold franchises there, kept the largest share of the royalties, and passed the remainder up to the master group in Toronto.

How did you transition back into operating a lawn care franchise yourself?
Terry: When I sold to TruGreen, I had a three‑year non‑compete that restricted me from operating in the cities where I had locations — places like Madison, Appleton, Green Bay, Lexington and Peoria. Once that non‑compete expired in January 2001, I re‑entered the business as a Weed Man franchisee. I started the Madison operation with one of my wife’s nephews, and when he chose to pursue something else, we hired a manager.

That’s around the time Andy, who had been helping me sell during college, stepped in and ultimately became the manager in Madison. From there, Andy and I began working closely together, growing the business organically into new markets and then merging additional markets into our holding company over time. Our first billing year in Madison in 2001 was about $110,000 in revenue; today, we’re around $103 million, so it’s been quite a run over roughly twenty‑five years.

Secrets to scaling Weed Man

What are your secrets to growth? How do you scale from $110,000 to $103 million?
Terry: A big inflection point was when I met Roger Mongeon, who held the U.S. rights to Weed Man and is one of the smartest people I’ve ever met, both in business and in general. He’s a former chemical engineer, and we developed a deep mutual trust and respect. He showed me the systems Weed Man had built, and I quickly realized that to handle significant growth, you must have robust systems. People talk about breaking through glass ceilings in their careers; growth in a business is similar — you can’t get to the next level without systems that ensure nothing falls through the cracks as you add people and locations. You also need a relentless attitude — failure can’t be an option.

Take me back 26 years. What did that very first Weed Man location look like day to day, and what convinced you both that it was worth betting your careers on?
Andy: From my perspective as a college kid at the time, I wasn’t initially thinking of a long‑term career. I’d show up on Saturdays to an almost vacant shell of an office and be the only person there selling lawn care. We used old‑school telemarketing to generate leads, and my cousin, who had started the business with my dad, was out treating lawns nearly by himself.

That first year, revenue was around $100,000, so there simply weren’t many people involved. Each year, as we added revenue, we’d bring in another technician, then another and eventually a senior technician, gradually building out the team.

Solving mistakes

Andy, can you share an instance when you made a mistake running the company and how you fixed it?
Andy: Early in my leadership career, I was wearing 10 hats and constantly chasing people around. When we first introduced door‑knocking for lead generation, I found myself running after supervisors every morning because they kept forgetting door hangers. One day, I realized how unsustainable that was. Instead of continuing to chase people, I focused on developing better systems — start‑of‑day procedures, checklists and clearer role ownership — so that team members owned their responsibilities. That experience was a catalyst for me to shift from being a task‑oriented manager to a leader focused on developing other leaders.

Hand-raising culture

Andy, you have described the organization as having a hand-raising culture. What does that mean?
Andy: Hand‑raising culture describes leaders inside our organization who literally raise their hands to take on new challenges and uproot their lives. For example, a gentleman from Green Bay volunteered to move to Austin to start that branch, and another teammate from Madison, who had also worked in Milwaukee, raised his hand to move to Denver.

Those markets are now among our top performers — Denver, for example, grew from around $250,000 in first‑year revenue to over $8 million. We keep building stables of leaders who breathe our mission — people, opportunity, community — in that order. They buy into that mission and carry it into their branches and departments, which creates new opportunities in new areas and truly changes lives. Many people in our company have careers they never imagined, and they, in turn, pass that mindset to the people they lead.

Long-term vision

What are your plans for growth and succession?
Andy: We plan to keep doing what we do best: changing people’s lives for the better and building a culture where people want to advance that mission of people, opportunity, community. If our people are taking care of each other and building something they can call their own, we’ll be fine.

Terry: At the system level, Weed Man as a whole generates around $435 million to $450 million in annual revenue, and with Epic3 at around $103 million, we’re a significant contributor. The broader goal is to become a billion‑dollar company, and we want to help drive that by innovating and supporting other franchisees within the Weed Man family. Together, we intend to reach that billion‑dollar milestone while maintaining the culture and systems that got us here.

Terry Kurth, 77, says that choosing the right life partner is the most important decision an individual can make — and he knows the truth of this statement firsthand. Nearly 50 years ago, his wife was in labor. She was in the hospital lying on her side with severe back pain because their daughter, Amanda, was turned 180 degrees in the womb.

Terry was there for his wife — but he also didn’t stop working. 

“I had one hand on the small of her back to relieve pain and the other on the phone calling prospects to sell lawn care,” Terry tells Entrepreneur in a new interview. “She didn’t complain because she knew we were about to have another mouth to feed, and failure wasn’t an option.”

Talk to any founder, manager or entrepreneur right now, and you will hear the same word. Overwhelm. People are trying to keep up with a pace that never slows.

AI is reshaping industries before leaders can absorb the last change. Even the high performers who usually stay calm under pressure say they feel stretched thin. Leadership capacity is dropping at the exact moment when demands are rising. Many workplaces feel like they are running out of room to breathe.

Overwhelm is not a personal failure. It is a structural reality. Leaders are trying to make good decisions while the ground keeps shifting under them. Economic conditions change without warning. New tools appear faster than people can learn them. Policies and regulations move in ways that force teams to rethink plans they made only days earlier. Supply chains wobble and require constant recalibration. The volume of change is so high that even experienced leaders feel like they are running a race where the course keeps moving.

I kept thinking about this during marathon training. The breakthrough didn’t happen during a long run. It happened on a rest day. Training had a rhythm. Some days focused on endurance. Some days focused on speed. Some days focused on strength. And then there were planned days off, which were just as important as the work. That recovery is the missing piece in today’s workplace. Most leaders operate in environments that never pause and never reset. Overwhelm keeps building because there is no chance to regain capacity. We cannot slow the world down, but we can learn to move through it with steadiness. That is the work of endurance.

Why this matters now

Overwhelm is becoming the defining condition of modern work. The pace of change is now faster than the pace of human adaptation, and that gap is widening. AI is accelerating decisions, expectations and competitive pressure. Markets are shifting in weeks instead of quarters. Teams are being asked to absorb more information than their cognitive systems were designed to handle.

Leaders who do not adjust will see slower decision cycles, rising conflict and declining performance. The organizations that thrive will be the ones whose leaders build endurance skills that match the speed of the environment. This is not about surviving chaos. It is about learning to operate confidently inside it.

What overwhelm looks like for leaders today

The familiar challenges are still here. Work-life balance. Office politics. Managing personalities. Endless decisions. Constant context switching.

What is new is the speed and instability surrounding them. One colleague told me, “The strategy we launched on Monday doesn’t work by Wednesday.” Another said, “I’m not between a rock and a hard place. I’m in a rock tumbler.” These comments are not exaggerations. They are honest descriptions of what overwhelm feels like in real time.

Leaders need a training plan for a world that does not include rest days. Endurance comes from small, repeatable practices that help you stay steady under prolonged strain.

Below are five endurance skills that reduce overwhelm at the source.

1. Reduce cognitive load at the source

Most leaders try to manage overwhelm by working harder. Endurance leaders reduce the inputs that create overwhelm in the first place.

Practical moves:

• Shrink the number of priorities in play at any moment.
• Collapse decision pathways so teams know exactly how choices get made.
• Remove optional meetings and optional reporting.
• Standardize anything that repeats.

This is not time management. It is load management, which is the real antidote to overwhelm.

2. Shorten the distance between signal and action

Overwhelm grows when leaders sit in ambiguity. Endurance leaders shorten the time between noticing a problem and addressing it.

Practical moves:

• When something feels off, act within twenty-four hours.
• When a project drifts, reset expectations immediately.
• When a team is confused, clarify the path the same day.

This prevents small issues from becoming system-wide strain.

3. Build a recovery rhythm into the workweek

Most leaders think recovery is a luxury. Endurance leaders treat it as infrastructure.

Practical moves:

• Protect one meeting-free block every day.
• Add a weekly capacity check with your team.
• Use microbreaks to reset your cognitive system before it hits overload.

Recovery is capacity maintenance, not rest. It keeps overwhelm from compounding.

4. Practice emotional neutrality under pressure

Overwhelm spikes when leaders absorb the emotional intensity of the moment. Endurance leaders stay neutral long enough to choose a response.

Practical moves:

• Notice your first reaction and delay it by sixty seconds.
• Label the emotion without acting on it.
• Respond only when your heart rate drops.

This is emotional regulation, which is the foundation of endurance.

5. Anchor every decision to purpose

Overwhelm grows when leaders lose sight of the destination. Endurance leaders use purpose as a filter.

Practical moves:

• Ask whether the work moves you toward the mission before saying yes.
• Remove tasks that do not serve the purpose.
• Reconnect your team to the mission weekly.

Purpose is directional clarity. It cuts overwhelm in half.

The world is moving fast. You can still finish strong.

A world without enough rest breaks is not ideal. But it is the world we have. Leaders need endurance. Not the heroic kind. The practical kind. The kind built through small habits that help you stay steady in a world that keeps accelerating.

These practices will not slow the world down. They will help you move through it without losing yourself. And they will help you lead others who are feeling the same overwhelm you are.

Talk to any founder, manager or entrepreneur right now, and you will hear the same word. Overwhelm. People are trying to keep up with a pace that never slows.

AI is reshaping industries before leaders can absorb the last change. Even the high performers who usually stay calm under pressure say they feel stretched thin. Leadership capacity is dropping at the exact moment when demands are rising. Many workplaces feel like they are running out of room to breathe.

Overwhelm is not a personal failure. It is a structural reality. Leaders are trying to make good decisions while the ground keeps shifting under them. Economic conditions change without warning. New tools appear faster than people can learn them. Policies and regulations move in ways that force teams to rethink plans they made only days earlier. Supply chains wobble and require constant recalibration. The volume of change is so high that even experienced leaders feel like they are running a race where the course keeps moving.

Most founders who eventually find success remember their major accomplishments. But they also remember their close calls: the times when things almost fell apart because of knowledge gaps, missing resources, a lack of support or simple bad luck.

Most of us tell ourselves that if we’re ever in a position to set other entrepreneurs up for success, we’ll make sure they have the training, education and networking opportunities we didn’t have. But not every well-intentioned entrepreneur ends up with that chance.

When I set out to create Roof Maxx with my brother Todd, our main goal was to provide an alternative to roof replacement for homes with aging asphalt shingles. But along the way, we discovered a golden opportunity to educate members of the roofing industry and provide resources to help contractors across the country improve their services.

As former roofers who spent 15 years struggling to survive in the industry ourselves, that had personal value to us beyond what it achieved for the business. Here’s how the dealer network we established to scale our company also helped us give back to our community, and what it taught me about empowerment.

Setting people up for success is usually a resourcing issue

I will be the first person to tell you that culture and core values play an important role in mentorship. You want to create a supportive and productive environment that facilitates healthy growth. But all of that is just wishful thinking if you aren’t willing to put your money where your mouth is.

This can look different depending on how your company is structured. In a company where most of your employees are on salary, that might look like investing in paid training and upskilling opportunities or ensuring that department heads have the budget they need to comfortably and consistently hit KPIs so that they don’t experience widespread burnout and unsustainable turnover.

Roof Maxx isn’t built that way. Our dealership model means the roofers who carry our product are independent contractors who purchase it from us so they can sell restoration services to their customers. They’re not on our payroll, but we still have a responsibility to help them succeed because they’re our most effective brand ambassadors.

So for us, resourcing looks like investing in training and support. Roof Maxx Connect, our proprietary dealer management software, was expensive to develop and doesn’t generate a dollar of direct revenue. What it does do, however, is streamline the same tasks for our dealers that Todd and I found most grueling when we were roofers: handling leads, managing warranties, training with Roof Maxx University and more.

Dealers who have that kind of support are more efficient and provide more consistent service, which helps them sell our product and makes them more likely to keep purchasing it from us. As a former roofer who was once responsible for handling all those tasks independently and who almost went out of business, I see the impact every day.

Valuable partnerships depend on mutual benefit

Over the course of your career, you’ll probably meet at least a few businesspeople who think every deal needs to have a winner and a loser. I don’t just think this attitude is simplistic; I think it’s self-defeating.

This kind of win-lose bargaining strategy depends on securing concessions from others, which in practice means forcing them to settle for less. That may help you acquire short-term gains, but it is not a recipe for respectful and lasting partnerships. In my experience, people who think you’ve given them a raw deal tend to remember it, and they are rarely inclined to go the extra mile on your behalf.

Our dealers carry the Roof Maxx product, but they’re partners rather than subordinates. They don’t carry it because they have to; they choose to carry it because it allows them to offer genuine value to the homeowners they serve. In turn, we make a commitment to keep earning their business by working to ensure that our product remains competitive and effective. This is one of the primary differences between the kind of dealer model we rely on and a franchise.

Oversight is not the same as surveillance

As a roofer, Todd and I were personally involved at every level of our business. With Roof Maxx, we can’t afford to be.

Our dealership network currently extends across North America. Even with Roof Maxx Connect, it’s impossible to have total visibility into every single thing our dealers do — but more importantly, we don’t need to.

When you run a small business, handling everything yourself is a practical strategy for quality control. When you’re an eight-figure national brand, it’s a recipe for founder burnout. Moreover, forcing your dealers — or employees, if that’s how your company operates — to report their every move to you creates unnecessary operational obstacles for them and eventually causes friction in those relationships.

Thanks to our platform, we know how leads are being routed. We can see how invoices are fulfilled, check to see whether individual dealers have policies that comply with applicable laws and industry regulations, and view reports of completed jobs. We don’t need more than that, and to ask for it would put a stumbling block in the way of people we need as much as they need us.

At the end of the day, the best ways to empower an entrepreneur are by investing tangible resources in the tools they need, grounding your relationships on a foundation of mutual respect, and trusting their expertise. Every contractor I can give that to via Roof Maxx is someone I can trust to go out every day and improve the state of the industry for all of us.

Most founders who eventually find success remember their major accomplishments. But they also remember their close calls: the times when things almost fell apart because of knowledge gaps, missing resources, a lack of support or simple bad luck.

Most of us tell ourselves that if we’re ever in a position to set other entrepreneurs up for success, we’ll make sure they have the training, education and networking opportunities we didn’t have. But not every well-intentioned entrepreneur ends up with that chance.

When I set out to create Roof Maxx with my brother Todd, our main goal was to provide an alternative to roof replacement for homes with aging asphalt shingles. But along the way, we discovered a golden opportunity to educate members of the roofing industry and provide resources to help contractors across the country improve their services.

Every successful business relies on policies and procedures. Policies and procedures create consistency, improve quality and allow organizations to move in a unified direction.

For this reason, most successful companies have policies and procedures manuals and other written policies. Without them, companies become chaotic and inconsistent as they grow. But there is an important distinction between systems that are intentionally designed and those that simply evolve over time.

The most damaging policies in a business are often the ones that were never actually created.

These can be called made-up rules — unwritten practices that slowly become accepted as official policy, even when no owner, executive, or person with authority ever approved them. They emerge quietly and gradually. An employee assumes something is required in every circumstance. Another employee observes that behavior and repeats it. Before long, an entire department believes a process is a mandatory policy when, in reality, it is not at all.

As organizations grow, these unofficial rules have a way of growing. Each one may seem insignificant on its own, but together they create a layer of legalism that slows decision-making, frustrates employees, delays customer service and quietly limits growth. It can also upset employees by creating an abundance of rigid rules that make the employees feel restricted. Unlike obvious problems such as declining sales or rising expenses, these self-made policies and procedures are rarely visible on a financial statement. Yet, their impact can be enormous.

Good intentions can create bad processes

One of the biggest challenges is that these rules often originate from good intentions. An employee wants to avoid making a mistake, so an extra rigid rule is added to prevent a situation from repeating itself. In other instances, someone encounters an unusual circumstance and begins treating that exception as the standard procedure. Over time, isolated events become permanent rules that harm, not help the company.

The problem is that businesses rarely struggle because of one unique situation. Instead, hundreds of small, unnecessary rules accumulate over months and years. Each additional email, approval, signature, or verification adds only a minute or two. Standing alone, that seems inconsequential. Collectively, however, those minutes become hours, days and eventually weeks of lost productivity, revenue or efficiency across an organization.

Imagine an employee who must wait for an internal confirmation before beginning work, even though all of the information needed to proceed is already available. Perhaps no owner, CEO or senior leader required this waiting period. It simply became “the way we’ve always done it.” If that delay happens dozens of times each week across multiple employees, the organization begins paying people to wait rather than to produce. Customers experience slower service, revenue decreases and management wonders why the business feels less efficient despite hiring more people.

Growth often brings more red tape

This scenario becomes even more pronounced in growing companies. Startups often move quickly because communication is simple and decisions are made by a small group of people. As headcount increases, however, there is a natural temptation for mid or lower level employees to add more approvals, more meetings, more documentation and more checkpoints. While some of these additions are necessary, many are simply reactions to isolated situations rather than thoughtful improvements to the business as a whole.

Over time, employees begin confusing caution with excellence. Instead of asking, “What is the best way to accomplish this?” they begin asking, “What is the safest way to avoid criticism?” Those are fundamentally different questions. The first encourages innovation and efficiency. The second often produces bureaucracy and red tape out of a desire for self-protection.

Perhaps the most dangerous aspect of made-up rules is that no one takes responsibility for them. Ask employees why they follow a particular procedure, and familiar responses usually emerge: “That’s just what we’ve always done,” or “I thought that was company policy.” Continue asking questions, and it frequently becomes clear that no one can identify when the rule started or who authorized it. The process has simply taken on a life of its own.

Challenge every unwritten process

Business owners should periodically examine their organizations with fresh eyes. Rather than asking employees whether they are following procedures, leaders should ask why those procedures exist in the first place and who authorized them. Every recurring process should have a clear purpose. If no one can explain why a particular step is necessary, it deserves careful scrutiny. In many cases, the unwritten rule should be disavowed and eliminated.

One effective exercise is asking managers to identify the biggest obstacles that slow their teams each day. Their answers are often revealing. Employees are rarely frustrated by hard work. They are frustrated by preventable delays — waiting for approvals, tracking down information, duplicating work or complying with procedures that no longer serve a meaningful purpose. These bottlenecks consume time without creating additional value for customers or employees.

It is also important to recognize that removing unnecessary rules does not mean lowering standards. High-performing organizations absolutely need accountability, quality control and thoughtful procedures. The goal is not to eliminate structure. The goal is to eliminate red tape that adds complexity without improving outcomes. Every policy should either reduce risk, improve quality, enhance the customer experience or increase efficiency. If it accomplishes none of those objectives, or it creates more problems than it helps, it is reasonable to question whether it should continue to exist.

Speed is a competitive advantage

Business leaders often focus tremendous energy on generating more revenue. They invest in advertising, marketing, recruiting and technology to accelerate growth. Yet, they sometimes overlook the operational drag occurring inside their own organizations. A company can spend millions of dollars attracting new customers while simultaneously slowing those customers’ experience through unnecessary internal processes. Removing friction is often one of the least expensive — and most profitable — ways to improve performance.

In today’s competitive environment, speed has become a meaningful differentiator. Customers have more choices than ever before, and they increasingly expect prompt responses, efficient service and straightforward interactions. Organizations that eliminate unnecessary delays position themselves to deliver a better experience without spending additional money on customer acquisition.

The best leaders understand that their role is not simply to create new policies. It is also to challenge existing assumptions. They recognize that every process should earn the right to continue existing—and should not be professed as policy without the company specifically authorizing it. As businesses evolve, procedures that once made perfect sense may become outdated. Failing to revisit them allows yesterday’s solutions to become tomorrow’s obstacles.

Eliminate the unnecessary rules

Every organization accumulates unwritten rules over time. Meetings become longer, approvals become more numerous and workflows become increasingly complicated. Left unchecked, these changes gradually reduce the agility that once fueled growth. Successful companies recognize that maintaining operational excellence requires periodic auditing and removal of these unwritten rules. Just as businesses routinely evaluate expenses, marketing efforts and financial performance, they should also evaluate the rules employees create or follow every day.

Sustainable growth is not achieved simply by working harder or hiring more people. It is achieved by creating an organization where talented employees can perform meaningful work without being slowed by unnecessary red tape. The companies that consistently outperform their competitors are often not those with the most elaborate systems. They are the ones disciplined enough to remove the systems that no longer serve a purpose.

Sometimes the greatest improvement a leader can make is not introducing another policy. It is eliminating unwritten rules that were never approved in the first place.

Every successful business relies on policies and procedures. Policies and procedures create consistency, improve quality and allow organizations to move in a unified direction.

For this reason, most successful companies have policies and procedures manuals and other written policies. Without them, companies become chaotic and inconsistent as they grow. But there is an important distinction between systems that are intentionally designed and those that simply evolve over time.

The most damaging policies in a business are often the ones that were never actually created.

A financial planner named Ted Jenkin coined a term recently that I haven’t been able to stop thinking about.

Lifestyle loopers.

He uses it to describe a rapidly growing population of Americans between 30 and 50 who earn six figures and are somehow still going nowhere financially. Every raise gets absorbed. Every bonus evaporates. The income climbs. The wealth doesn’t.

I’ve watched this pattern play out for years through SparkRental and the Co-Investing Club. Smart, capable people with impressive salaries who, when you look at their actual financial picture, have very little to show for it. Not because they’re reckless. Because they’re caught in a loop they can’t quite see from the inside.

Lifestyle creep is not a new concept. The idea that spending rises with income is well documented. But what doesn’t get talked about enough is how completely natural and justified each individual step feels.

You get a promotion. You move to a better apartment because you can now afford it, and the old one was genuinely a bit cramped. Reasonable.

You get another raise. You lease a better car because your commute is long and you spend a lot of time in it. Reasonable.

Your income climbs further. You start eating out more, traveling more, upgrading more. Each decision is defensible on its own. Together, they form a structure where your expenses perfectly track your income, and the gap between what you earn and what you accumulate stays exactly the same.

The Goldman Sachs finding that about 40% of people earning over $500,000 a year report living paycheck to paycheck isn’t about irresponsibility. It’s about structure. When spending is the default and saving is the afterthought, income alone doesn’t determine financial progress. Behavior does.

Most financial advice treats this as a discipline problem. Track your spending. Cut the subscriptions. Stop eating out so much. Set a budget and stick to it.

The problem is that this advice fails consistently for high earners. Not because they lack discipline in other areas. Because budgeting and willpower are reactive systems. You’re fighting against the current every month, deciding in the moment whether to spend or save.

And in any given moment, spending usually wins. It’s immediate. It’s concrete. The benefit is right there. The cost of not saving is abstract and distant. Even people who know exactly what compound interest looks like in 20 years still spend the money today.

This is not a character flaw. It’s how human psychology works. We’re wired to prioritize the present. Every financial decision is a battle between the person you are now and the person you’ll be in 20 years, and the person you are now has a significant home-field advantage.

The only reliable solution to a behavioral problem is to remove the behavior from the equation entirely.

Pay yourself first is the phrase. Automate the savings. Move the money before you feel it. The version of this that actually works for high earners isn’t a monthly transfer to a savings account you can see and access. It’s routing capital into something that genuinely locks it away.

This is one of the reasons illiquid investments have a real advantage over liquid ones for people with good incomes and lifestyle-creep tendencies. When the money is in an index fund you can sell in two clicks, the temptation to deploy it for something else exists constantly. When it’s committed to a three-to-five year real estate investment, that temptation is gone. The decision was made once, up front, and the money is doing its job in the background while you get on with your life.

I’ve seen this dynamic firsthand through the club. Members who describe themselves as poor savers but have done remarkably well as passive investors, because the investment commitment removes the daily friction. The money leaves. It works. Distributions arrive. The loop breaks.

Ashley:
Most people spend 40 years working so they can stop working, but what if you could build a life where work is optional way before 65?

Tony:
Ashley and I are pulling back the curtain today on our actual retirement plans, what we’re doing, why we’re doing it, and what we wish we would’ve known sooner because no one handed us a roadmap. And if you’re a real estate investor trying to figure this out on your own, well then this episode is for you.

Ashley:
This is the Real Estate Rookie Podcast. I’m Ashley Kehr.

Tony:
And I’m Tony J. Robinson.

Ashley:
So I have actually put together a list of questions for Tony and I to actually go through to share our own journey saving for retirement. And hopefully this will help a lot of you be able to plan for your own retirement. So Tony, the first thing I kind of want to go over is the beginning. When were we first introduced to retirement? And I think for me, it was when I graduated college and I started my first job and I got a 401k with that first job.

Tony:
Yeah, I think same for me. And I’ll just add context for the entire audience that between me and Ashley, Ashley’s definitely the resident retirement expert between the two of us and she educates me on a lot of these things. But yeah, I think it was for me too. When I graduated college, actually my first job after college did not offer a 401k and that job did not last very long, but my first real big boy job after college I think was a few months afterwards. And yeah, I got a 401k and I had to sit there with my other coworkers who were recent college grads and were trying to figure out, okay, how do we put these percentages there and what does this mean? But yeah, it was a first job after college with the 401.

Ashley:
Yeah, my first job only lasted six months, my accounting job before I quit and went into property management. But from that first job, I had very little vested. So a lot of times a 401k, you have to work there for so many years before they’ll actually give you the employer contribution of it. So it was very little. And when I left there, I ended up rolling it over into a Roth IRA. Still really didn’t know a lot about retirement at all. It was actually a friend that told me and helped me go through that. I didn’t really know a lot about it. And I actually had a financial advisor then. So after I had left that job, the new investor I started working for, the property management company had a financial planner. I was like, “This is probably a good idea for me. ” And I went to him and all I had was my little money.
Honestly, it was probably like $500. I don’t remember. But it rolled over into that. And then we just did some financial planning of what to do for the future. And I probably had the financial advisor for maybe five years. One thing he did do for us was set up 529 plans for the kids, which we’ll talk about that more later. But other than that, I really didn’t use the financial planner at all. I think it was like $700 to $1,000 just to meet with him and go over stuff and definitely was not worth the money. And then my second job, I didn’t even get any benefits at first. I worked there for several years. I was part-time. I worked whenever I wanted. And it actually came to a point where I asked for benefits and I got health insurance and then I got 401. And I believe it was a 3% match and I had to contribute 3% for them to give me that match, which is pretty common.
So Tony, do you remember at Tesla at all when you would, did they have a match at all?

Tony:
Yeah. So Tesla was slightly different, but I’ll go back to that first job. I actually worked for Target before working at Tesla and Target did have a match. I don’t remember what it was. It was so many years ago at this point, but I remember I just invested up to that match, whatever the match was, that’s what I invested up to. So I maxed it out there and I can’t remember what it was, but that’s what I did at Target.

Ashley:
So kind of our next investment for retirement, which we really probably didn’t think of it at the time, but was purchasing our rental properties, my long-term properties and your short-term rentals. So Tony, at the time that you were going to ignore your long-term rentals because you sold them, but your short-term rentals, when you were purchasing those, did you have anything in your mind thinking about this, I will use these properties for retirement? In any sense, were you thinking about that down the road?

Tony:
I mean, that was really the main reason that I got into real estate was because my dad growing up always said, “Unless you want to get up and go to a job every single day until you’re much, much older, you’ve got to have some assets that pay you on a regular basis.” And he’s like, “Real estate’s one of the best ways to do that. ” So that was just drilled into me very, very early on. So I don’t know if I thought about it as retirement, but for me, it was just always having that financial freedom, I guess, more so. And that’s what pulled me into real estate to begin with.

Ashley:
Yeah, that was definitely my framing and thinking too, but it was more like now. How can these assets give me the financial freedom now as in retired? But we all know landlording, short-term rental operations, a lot of that isn’t a quiet retirement sailing off into the sunset. There’s still a lot of work to do, but I never thought about what… I knew I wanted to hold properties long-term, but I never actually saw what mortgage pay down appreciation and an increase in rental income every year can actually do to just be a ton of equity by the time I’m 65. Hopefully a ton of equity before that. I have to say that it probably took me about eight years before I actually really started strategizing what properties I was keeping and which ones I was selling to think about later on in life. So I wanted to think about which properties would have a lot of appreciation where I would have options with them.
Where before, when I first started investing, it was a cashflow play. I didn’t care if they appreciated, I just wanted cashflow. Well, some of those properties were like $20,000 duplexes, but they cash flowed a lot, but they were headache properties. They were in areas that saw no appreciation. I was super, super lucky where I bought them at the right time and I sold them just after COVID when prices went crazy. And so I was able to sell them and get rid of them at a good time. But even if I would’ve held onto them for a long time, the appreciation just wouldn’t be what it was for other areas where I went for higher dollar amount properties in better areas, better school districts and things like that. So as I’ve started to weed out my portfolio, I put a lot of thought into down the road in the future.
I want salable assets that I have a easy exit strategy. They’ll have a lot of equity built up into them and I can tap into that at any time that I need to. Tony, what about you? Have you kind of changed or pivoted your strategy at all thinking more about the future when you’re ready to just retire?

Tony:
Not necessarily. I mean, I think we’ve been fortunate enough that I think the long-term prospects of all the markets we’ve invested into, we’ll probably continue to see pretty good appreciation, like a good chunk of our portfolios in California, which typically does pretty well. So I don’t know if we have anything that we’ve purchased where I question it’s the long-term viability in the portfolio. There are some properties that are just like headaches for other reasons, but I truly think if I hold all these properties for 30 years, we’ll probably be in a pretty good position in terms of loan paydown and appreciation.

Ashley:
We’re going to take a short break, but when we come back, we’re actually going to go through the retirement stack. And this is from Scott Trench from BiggerPockets Money. And this is going to tell you multiple options of what you can do for retirement and his recommended order of how to invest in these things. So we’ll be right back. Okay, welcome back. So we got into a little bit about Tony and I’s real estate for retirement, but we also want to talk on other investment vehicles that you can do for retirement because it is important to diversify and there are a lot of advantages to using some of these other retirement vehicles. I was listening to a podcast the other day with Scott Trench and Mindy Jensen on BiggerPockets of Money, and Scott went through and put together his retirement contribution order of operations. So this was for specifically a high-income W-2 household, but really I think this would work for any W-2 income household.
And if you are self-employed, you’re not going to get an employer 401k match, but you could still go through these orders of operations in some sense, but obviously you’re not going to be able to have access to all of them. But also there will be other options for you too because you are self-employed and don’t have a 401 employer option available to you. Okay, so the first one is take your employer 401 match because this is in a sense free money, but I mean technically it’s worked into your compensation package, but you should take it. Don’t leave it on the table because that’s money lost. So sometimes you don’t have to contribute, you just automatically get the match from your employer. So that’s even better. But that is step number one is to take that.

Tony:
Step number two, and this is the one that literally changed my life, but it’s the employee stock purchase program or ESPP where companies allow you to buy stock at a discounted rate. So again, I spent the majority of my W-2 career working at Tesla and I was very fortunate that during that time the company did incredibly well in the stock market. And we were able to purchase from every paycheck that would take out however much you wanted to allocate, but you could buy Tesla shares at a 15% discount. So just imagine the amount of wealth you’re able to build of every single paycheck. I think we were paid biweekly. So it was at 26 times a year I was able to go out and buy Tesla stock at a 15% discount while the stock was also increasing at this pretty rapid pace. And gosh, I want to say I might be confusing the bonuses with the employee stock purchase, but I want to say that there was a fixed price that you would be able to buy it for the quarter.
So even if it went up a little bit, you still even got maybe a bigger discount. But either way, for me, that’s where I put the majority. I think I was just putting in to match at Tesla as well for the 401k. Actually, I don’t even know if Tesla offered a match. I really can’t remember because I know most of my money was going into ESPP because that’s where I saw the biggest opportunity. But guys, when I lost that job, it was all of that stock that I’ve been piling into for years and years at that point that allowed us to have the foundation to build our portfolio and go full-time into real estate. So truly one of the best returns that I’ve ever had on any investment.

Ashley:
Yeah, I’ve never worked anywhere that had that as an option. So the next one, step three is to max out your HSA. So I believe not everyone can actually get an HSA. You usually have to be in a high deductible plan, but with the HSA, you’ve put in pre-tax money and it gross tax-free. And if you use it for medical, it’s tax-free when you pull that money out too. So it’s like a triple tax advantage. So this is great to save as you get older. You may have more medical expenses in your elderly age and you’ll have all this money to pull out tax-free to be able to use. Also, even now as you have medical things that come up, but to pay your deductible for your high deductible plan and other medical bills that you may have that you can use that money for.
But that’s a huge advantage because it’s like a triple savings on taxes right

Tony:
There. And 7.4 is to max out your dependent care FSA. I’ve actually never used this before and I’ve had kids almost my entire life now at this point and I’ve never used this. Are you using a dependent care FSA at all, Ash, or have you used one in the past?

Ashley:
No, I’m not. So it’s like a pre-tax employer sponsored. So again, if you have a W-2 job and your employer has to offer this, but it’s used to pay for childcare expenses.

Tony:
My brother-in-law works for a global tire distribution company and they offer an FSA and that’s how he pays for his babysitters through that account or for his nanny through that account. So just a good way to save on taxes on something you’re going to spend money on anyway.

Ashley:
Okay. So step five is to max your 401 contributions. So as of 2025, if anyone’s still filing those tax returns for 2025, the max contributions you could do is up to 23,500. So this is pre-tax contributions. And I mean that’s a lot of money for a lot of people to be able to put $23,500 after you’ve already contributed to a lot of these other things too. So this would be just maxing out your 401k.

Tony:
Ash, I’ll let you take maybe six and seven just because I feel like I can’t speak confidently to the IRAs.

Ashley:
Okay. Then the next thing is the Roth IRA. But this is if you are a high net come earner, you’re not eligible for an IRA. So for single head of household, you have to be $153,000 or under. You can’t make more than that. If you’re married filing jointly, it has to be under $242,000 to be able to contribute into the Roth IRA. The Roth IRA is where you contribute after tax income and then your money grows tax-free. One thing I really like about the Roth IRA is that really at any time, unless you’re using an employer sponsored plan, they may not allow this, but if you just go to Vanguard, Fidelity, open your own account, what you contribute, you can pull out at any time tax-free and penalty-free because you already paid taxes on that money when you put it in there. So you want a down payment for a property and you have the money that you’ve contributed over the years in a Roth IRA, so you’ve contributed $50,000, maybe it’s grown to 70,000, you could pull out 50,000 of that and use it for a down payment on a rental property.
So that’s what I like about the Roth IRA is you can still access that money without having to pay any penalties or fees. If you do make over that amount of money and aren’t eligible for a Roth IRA, there is something called a backdoor Roth IRA. And first of all, I’m going to urge you to go over and listen to this episode of BiggerPockets Money. It was with Amanda Hahn, who’s a CPA, who talks about the benefits of how you could actually do a Roth IRA. But basically what you do is you’d contribute to a traditional IRA and then convert it immediately into a Roth IRA. And the limitation for 2026 for a Roth IRA is $7,500 that you’re able to contribute to it. Okay, then you can even take it a step further and do a mega to a Roth IRA. And once again, you have to check that your plan administrator allows this, but if you can make after tax contributions to your 401k, so it’s like a Roth 401k, then you can contribute it up to 72,000.
But then remember, this is a combined limit with what you’ve already put in, but then you can go ahead and convert that into a Roth IRA. And Amanda Hahn had said on this episode as to this is all legal, but it’s like the IRS, they always just make you jump through a hoop to get something done. It’s not like you can just easily go ahead and go into a Roth IRA. You have to do these hoops to be able to access this tax benefit. But talk to your CPA, talk to your financial advisor if these are options for you.

Tony:
And then the final step, step number eight here is the 529 college savings plan. And again, I’m 35. My son is 18, so it’s like more than half my life I’ve been a parent, but I didn’t even know about this when he was born. And now that we’ve got younger kids again, this might be something we end up using. But effectively, this allows you to take money after tax money. So you’ve already paid taxes on it. You can put this into this 529 plan and it grows and all of that growth is tax-free as long as it’s used for educational purposes. So sending your kid to college, to trade school, to apprenticeship program, something to that effect. And actually, I don’t know, Ash, do you know if there’s contribution limits on the 529?

Ashley:
It’s basically like a gift tax. So it’s 19,000 but 38,000 for married couples without having to report a gift tax.

Tony:
I mean, that’s a meaningful amount. If you’re doing that, you can send your kid to a very, very expensive school if you continue to do that over the course of their lifetime. So if you’ve got young kids, it is a great tool to allow you to set money aside and let it grow that you can then use for college.

Ashley:
So New York State, you can deduct if you’re individual up to 5,000. And if you’re married, you can deduct up to $10,000. So if that makes a big difference on your income tax return, but that’s another benefit depending on what state you’re in, it could reduce some of your reported income on your taxes for the state tax return. Another benefit of the 529 plan is I believe it’s 36,000 of that can actually convert into a retirement plan. So it actually convert into an IRA. So if the kids don’t use it for school, then you can actually save that money for their retirement and then they can pull it out when they’re at retirement age and they don’t have to use it for school. But there is a limitation, a cap on how much money can be used for that. But also the 529 plan, it can be used for private school, for high school, even I believe elementary too.
So even if you have a kid going to private school right now, you could contribute to it just to get the New York State tax write off, then pay the school out of it to have that deduction. But you can pay for books. I had seen this post before where it was an accountant that posted it on social media where they had said what you should do is put all this money into the 529 plan and then when your kids go to college, you buy a house there and have your kids use the money out of the 529 plan to pay you rent. So it’s guaranteed rental payments. The money that you contributed is coming back to you. One thing that people totally missed in the comments, and I actually started kind of arguing with someone, which I never ever engaged with. And the person who posted it finally responded like, yes, you’re absolutely correct.
Is that just remember that’s not tax-free money. That still rental income coming back to you. So you’re still paying taxes on that, but not as much as you would’ve when you first earned that money from your W-2 job.

Tony:
And then you do something like a cost segregation setting, you get some bonus depreciation and you qualify for rep status and material participation and you can still write off all those earnings, hopefully.

Ashley:
Okay. We’re going to take a short break and we’ll be right back after this to tell you what our plans are for the future for our retirement. Okay, welcome back. Thank you guys so much for watching or listening. If you haven’t already, make sure you are subscribed to our YouTube channel at RealEstateRookie. Okay, so we went over some retirement options that you may have, a recommended order of operations from Scott Trench, but let’s get into what Tony and I are actually doing now with these retirement options that are available and what we see for ourself down the road. So Tony, what is currently happening right now? Are you contributing to any kind of retirement plan that’s available out there?

Tony:
I do have a retirement plan. Yeah. Not a lot is in there because I just started it recently. I’m very overly concentrated in real estate right now. I still do have a Tesla stock for my time working there, but obviously that’s just one entity. So there’s still some risk there. I think that’s part of the reason I love when we talk about this is because you remind me there’s a lot of other options out there, but I think I get so focused on what’s in front of me and like, hey, real estate is a thing that I know so well, but there’s a benefit to having a diversified portfolio. So I think for me, it’s looking into some of these other options and seeing how I can expand those things.

Ashley:
I think too, real estate is so addicting. It’s like, okay, over the course of the year, I could contribute this money to a retirement account or even a brokerage account or whatever, or I could go and buy another property or I can add an upgrade to my short-term rental to increase the revenue there. Think about how many pools you put in. Those could have been money funneled into a retirement account for you, but that is your retirement, these properties too.

Tony:
But I think diversification is good. And I talk with a lot of folks who are coming from the opposite end where all of their retirement is in the stock market and they’re like, “Hey, I just want to diversify and have something that’s a little bit more tangible. And I’ve got so much that’s tangible that I probably need a little bit more that’s in the market.” So got to balance it out a little bit.

Ashley:
Yeah, I’m contributing right now to retirement plans and I maxed out my contributions last year, but this year I’ve been not as much. I’ve definitely slowed down my contributions just because like you said, there’s other things I want to do in real estate right now. So definitely not contributing to the max and I don’t think I’ll max out this year at all. But another thing is the 529 plans I did that financial planner, I guess maybe he was worth the $1,000 because I did contribute to my kids’ 529 plans when they were very little. And I think my oldest was two or three and then the other ones basically have them since they were born. And I’m pretty sure I’ve put, I think it’s like $50 a month I put in each one of them. And when I started them, I probably put in a thousand to fund them or something like that each maybe.
But they each have 12 to $14,000 in them right now at the age of eight, nine, and 12. So that makes a big difference being able to start and then if they decide not to go to college, you can actually change the beneficiary on them too. So I am the owner of the 529 plans, but at any time I could change the beneficiary. So actually my sister, she’s going to school right now to be a PA. And my aunt had money left in a 529 plan and she changed the beneficiary to my sister so she could use the money to finish out school. So that was really awesome. I

Tony:
Didn’t know that that was one of the features of the 529. Yeah. Are you able to use it for, say that you have a kid that wants to go to, they want to become a surgeon, so they’ve got to go to regular undergrad, medical school, residency, all those other things. Can you use it across all those different stages or does it stop at a certain stage? Do you know?

Ashley:
I don’t think it does. I don’t know for sure, but I’m pretty sure you can use it for any education. And that makes me wonder too, if you were a real estate agent, could you use it for your CE classes? Things like that. I’m not sure on the specifics of that. But one thing I like about it too is you can go into your 529 plan and you can print off little vouchers and you give these out to grandparents and say, “Hey, they don’t need another toy to clutter their house. Here’s a voucher. You can mail in a check and this will go into their 529 plan.”

Tony:
That’ll get all the kids excited on Christmas morning.

Ashley:
I mean, not that it’s worked for me yet. I haven’t noticed any increase in any of their accounts. It wasn’t Ruby, but that is an option out there. And I’ve read too a lot of articles about grandparents starting them also for kids and then they’re being the owners of it and then the kids being the beneficiary, the grandkids. So yeah, Tony and I are really interested as to how you are diversifying your retirement, what options you have available. One thing that’s been really important to me this year is financial opportunity and that is having many different ways to access capital. So if I have a medical emergency, I have a Roth IRA I can withdraw from. I have an investment property I can sell. I have a store full of liquor that I can liquidate going out of business sale. So I think that’s the biggest thing for me is I want to have financial options, not only in retirement, but now in life too.
So it’s been intriguing to me to talk about all these different ways to build financial freedom alongside real estate because I do think it is really important to diversify. Well, thank you guys so much for joining us. I’m Ashley and he’s Tony and we’ll see you guys on the next episode of Real Estate Rookie.