August 2026

The first quarter of 2026 was unlike any other in venture history. According to Crunchbase, investors poured $300 billion into startups globally in the quarter, up more than 150% year over year and an all-time record by a wide margin. AI drove nearly all of it: $242 billion, or 80% of total global venture funding, went to AI companies. The previous record was 55%. Four of the five largest venture rounds ever recorded closed in that single quarter.

The money has never been this concentrated this fast, or this focused on one category. But more capital flooding into AI doesn’t make fundraising easier for most founders. It makes it harder. Investors have more options than ever, and they’re using financial infrastructure — not just product quality — to separate the companies worth backing from the ones that aren’t ready.

I’ve spent more than 20 years advising high-growth and venture-backed companies, many of them AI and SaaS businesses. I’ve seen what separates the companies that move smoothly through major financing events from the ones that don’t. In almost every case, the technology is solid. The gaps are on the operational and financial side. And those gaps have a way of surfacing at the worst possible moment.

Here are four things investors scrutinize that most founders underestimate:

1. Whether your revenue model is as clean as your product

A strong revenue model generates revenue and makes sense to everyone in the room. Investors should be able to understand how your company makes money, why the model works and whether it can hold up at scale.

Some founders introduce complex, customized pricing structures to close early deals. That can work in the short term. But intricate customer terms and highly variable contract structures create real accounting and compliance challenges as the business grows. The same is true of other complexity triggers that accumulate quietly: enterprise contracts, international expansion, usage-based pricing models, complex financing arrangements. Founders often underestimate the accounting and compliance implications of each, and those implications are usually manageable until a financing, audit or diligence process puts the assumptions behind them under a microscope.

Stripe built its reputation on this principle from the start. Rather than layering in complex fee structures, it offered transparent, straightforward pricing that any developer or business owner could immediately understand. That clarity became one of its defining advantages, and a template that successful fintech and SaaS companies have followed ever since. Your model doesn’t have to be that simple, but it should be that clear.

2. Whether your margins actually improve as you grow

For AI companies, revenue growth alone isn’t enough. The question investors ask is whether the economics get better as the business scales, or just bigger. That means understanding gross margin after accounting for compute costs, model usage and infrastructure and being able to show that those margins improve over time as efficiency increases.

Equally telling is what’s happening inside your existing customer base. Strong net revenue retention — customers renewing, expanding usage and increasing spend over time — signals that the product is creating genuine value. According to High Alpha, companies with high net revenue retention grow 2.5x faster than their low-NRR counterparts, and those with exceptional NRR command premium valuations. If your customers aren’t expanding, investors will want to know why before they commit.

3. Whether you’ve built the governance infrastructure before you needed it

Most founders build governance structures when they’re forced to, whether by a new lead investor, an audit requirement or an exit process. The founders who handle those moments best are the ones who put that foundation in place before it is required.

Operational maturity doesn’t require a large finance team or a complex reporting package. It means you can produce reliable financial information, understand what’s driving the business, forecast cash with reasonable confidence and explain what has changed between periods and why.

When Builder.ai, once valued at more than $1 billion and backed by Microsoft and SoftBank, collapsed into insolvency in May 2025, it had been operating without a CFO since July 2023, leaving no senior financial steward to challenge projections or ensure reporting integrity. While the causes were broader, the absence of senior financial leadership became part of a larger story about weak financial oversight and reporting discipline.

One thing I tell founders frequently is to pay attention to what your board keeps asking about. The questions that come up repeatedly are usually the ones your reporting isn’t answering. That’s where to start building.

4. Whether you understand your risks as well as your opportunity

The founders who stand out in investor meetings can speak to the risk with the same fluency they bring to the product. Customer concentration, margin pressure, regulatory exposure, capital needs, competitive dynamics — the strong founders can talk about all of it with the same confidence they bring to the technology. That includes growth decisions that look like wins on the surface. Expanding into new products, markets or jurisdictions without fully understanding the tax, regulatory, compliance and reporting implications is one of the more common ways scaling companies slow themselves down. Those issues rarely show up immediately. But they do show up.

The same applies to forecasting. Boards know your budget is likely wrong before it’s approved. What they want to see is whether you understand which assumptions are most consequential and what you’ll do if things don’t go according to plan. That kind of clarity, owning the uncertainty rather than minimizing it, is what builds credibility.

Growing fast and growing well are not the same thing. The founders who grasp that distinction early are the ones investors want to back for the long term. The Q1 2026 numbers make clear that capital is available, more of it than at any point in venture history. The question isn’t whether AI companies can raise money. It’s whether yours is ready when the moment comes.

So before fundraising, founders should pressure-test the financial foundation investors will examine. Make revenue recognition and contract terms reviewable before diligence. Track gross margin after compute and infrastructure costs, not just top-line growth. Build board-ready financial reporting before a lead investor asks for it. And maintain a risk register or scenario model tied to cash runway, so the company can show how it will respond if key assumptions change.

The technology will get you in the room. The financial infrastructure is what keeps you there.

The first quarter of 2026 was unlike any other in venture history. According to Crunchbase, investors poured $300 billion into startups globally in the quarter, up more than 150% year over year and an all-time record by a wide margin. AI drove nearly all of it: $242 billion, or 80% of total global venture funding, went to AI companies. The previous record was 55%. Four of the five largest venture rounds ever recorded closed in that single quarter.

The money has never been this concentrated this fast, or this focused on one category. But more capital flooding into AI doesn’t make fundraising easier for most founders. It makes it harder. Investors have more options than ever, and they’re using financial infrastructure — not just product quality — to separate the companies worth backing from the ones that aren’t ready.

I’ve spent more than 20 years advising high-growth and venture-backed companies, many of them AI and SaaS businesses. I’ve seen what separates the companies that move smoothly through major financing events from the ones that don’t. In almost every case, the technology is solid. The gaps are on the operational and financial side. And those gaps have a way of surfacing at the worst possible moment.

Early in my career, I believed the hardest decisions could be optimized through detailed analysis, preparation and personal judgment. Then I faced a career transition that forced me to rethink that assumption.

I had earned a degree in a technical field and was considering a move into marketing. The opportunity was exciting, but I lacked the experience to fully understand what it would take to succeed in a completely different function. Fortunately, I had two people I trusted enough to ask for advice. One helped me understand the capabilities I would need to demonstrate to make the transition successfully. The other challenged my thinking and played devil’s advocate, surfacing risks I had overlooked. Neither told me what to do. Instead, they gave me perspectives that expanded my thinking and helped me make a more informed choice.

At the time, I never thought of them — or the ritual of consulting them — as part of a larger career strategy. Looking back, they became the first members of what I now call my personal board of directors. Over the last twenty years, that board has grown to six trusted advisors who have helped me navigate promotions, international assignments, leadership challenges and eventually entrepreneurship. Their greatest value has always been their ability to provide perspective in moments when my own experience was limited.

Why performance alone is rarely enough

One of the most surprising lessons I learned in corporate America is that strong performance and career advancement are connected, but they are not the same thing. Throughout my career, I worked with talented professionals who consistently delivered excellent results. They solved problems, earned strong reviews and became the most reliable members of their teams. Yet many of them struggled to gain visibility beyond their immediate managers.

Meanwhile, I watched others create momentum more quickly. As I paid closer attention, I realized they often had people behind the scenes helping them think through decisions. They gathered advice about what new skills to develop. Someone who had been there before showed them how to build relationships with influential stakeholders. They had mentors offering guidance, sponsors creating opportunities and trusted advisors helping them navigate challenges. Their success was supported by more than individual effort.

This is where a personal board of directors becomes valuable. It creates access to perspectives, experiences and relationships that would otherwise take years to develop on your own.

Build more than just mentors

Many professionals focus exclusively on finding a mentor. Mentorship matters, but relying on a single relationship creates limitations. Different people contribute different forms of value, which is why the strongest personal boards include a variety of perspectives.

Your board should ideally include:

• Mentors who share experiences and help you learn from challenges they have already navigated.
• Coaches who increase self-awareness and help you discover your own solutions.
• Sponsors who advocate for you with senior leaders and create opportunities.
• Peers who provide honest feedback because they see your strengths and weaknesses every day.

One of the biggest mistakes people make is assuming a sponsor, mentor and coach are interchangeable. They aren’t. Throughout my career, I’ve relied on different people for different needs — sometimes to challenge my thinking, other times to open a door, provide candid feedback or share lessons from a similar experience. Understanding the role each person plays helps you build relationships intentionally, rather than expecting one individual to meet every developmental need.

Identify the gaps first

Before deciding who belongs on your personal board, spend time understanding where you actually need support. Many people start looking for mentors before they have clarity about the guidance they need. A better approach is to begin with feedback.

One exercise I frequently recommend: ask five people for honest input. Choose two trusted peers, two colleagues from another department and one person with whom you’ve experienced some professional friction. Ask each the same questions about your strengths, development opportunities and overall effectiveness. The goal is to listen carefully rather than explain or defend.

When multiple people identify the same growth opportunity, pay attention. Those recurring themes often reveal where a mentor, coach, sponsor or advisor could have the greatest impact. Once you understand the gap, finding the right person becomes significantly easier.

Build relationships before you need them

Many professionals hesitate to reach out because they worry about appearing transactional. In reality, most meaningful professional relationships begin with curiosity rather than requests. The goal is to learn about the other person before seeking anything from them.

When I meet a leader for the first time, I often ask three simple questions:

• What is your role, and what does a typical day look like for you?
• How did you get here?
• What advice would you give someone earlier in their career?

These questions create authentic conversations while helping me understand whether the individual enjoys developing others and sharing lessons from their own journey. If the conversation goes well, schedule another one several months later. Strong professional relationships are built through consistency and genuine interest — they rarely develop from a single networking meeting or a sudden request for help during a career crisis.

Use your board during critical decisions

One of the most valuable uses of a personal board is during periods of transition. When I was considering leaving corporate America to pursue entrepreneurship, I reached out to three members of my board long before making the final decision. I wanted to understand how experienced leaders would approach a major life and career change.

What risks would they focus on first? How would they prepare financially? What actions would they take during the final six to twelve months before making the transition? Each person approached the challenge differently, which gave me a broader perspective than I could have developed on my own.

The purpose of a personal board is to help you see what you might otherwise miss. Every successful company relies on a board of directors to challenge assumptions and strengthen decision-making. Your career deserves the same level of strategic support.

Early in my career, I believed the hardest decisions could be optimized through detailed analysis, preparation and personal judgment. Then I faced a career transition that forced me to rethink that assumption.

I had earned a degree in a technical field and was considering a move into marketing. The opportunity was exciting, but I lacked the experience to fully understand what it would take to succeed in a completely different function. Fortunately, I had two people I trusted enough to ask for advice. One helped me understand the capabilities I would need to demonstrate to make the transition successfully. The other challenged my thinking and played devil’s advocate, surfacing risks I had overlooked. Neither told me what to do. Instead, they gave me perspectives that expanded my thinking and helped me make a more informed choice.

At the time, I never thought of them — or the ritual of consulting them — as part of a larger career strategy. Looking back, they became the first members of what I now call my personal board of directors. Over the last twenty years, that board has grown to six trusted advisors who have helped me navigate promotions, international assignments, leadership challenges and eventually entrepreneurship. Their greatest value has always been their ability to provide perspective in moments when my own experience was limited.

Every founder wants a moat. We spend countless hours discussing product differentiation, defensibility, AI, proprietary data and network effects. But after spending the last several years building a company in one of America’s least trusted, most opaque industries, I’ve come to believe we’ve been asking the wrong question. The most durable competitive advantage isn’t what you build. It’s whether customers believe you. 

In industries where customers feel confused, skeptical or taken advantage of, trust becomes the moat. But trust isn’t built through slogans or advertising. It’s built through operational decisions that customers experience every day. Unlike most competitive advantages, trust compounds. 

Why opaque industries create the greatest leadership test

Many industries remain opaque, not because they are inherently complicated, but because opacity has historically been profitable. Complexity creates leverage. If customers don’t understand how something works, they can’t easily compare offers, evaluate fairness or recognize hidden costs. Confusion does the heavy lifting. Businesses no longer have to earn trust because complexity protects them from scrutiny. That’s when companies begin optimizing for information asymmetry, margin extraction, low accountability and short-term transactions instead of long-term relationships. 

Gold is one example, but it doesn’t stand alone. Healthcare, car sales, real estate, financial services and online payments also often rely on opacity, leaving customers frustrated and wondering whether they made the right decision. The harder a market is for customers to understand, the easier it becomes for weak leadership to hide behind complexity.

This means rebuilding trust requires leadership, not better marketing.

The leadership decisions that build trust

When I started Alloy, I wasn’t trying to become “the transparent company.” I was trying to answer two questions:

• Who benefits from opacity?
• What breaks if we remove it?

The reason Alloy has earned repeat customers and word-of-mouth referrals isn’t that buying gold suddenly became easier. It’s not. It’s because we made leadership decisions that prioritized long-term trust over short-term convenience.

Transparency over margin maximization

Unlike many competitors, we chose to explain our pricing, process and expectations, even when doing so made negotiations more difficult. Conventional wisdom says transparency weakens your position because customers have more information. We found the opposite. When people understand how decisions are made, they’re more likely to trust the outcome, even if it isn’t exactly what they hoped for.

That philosophy led us to build online valuation calculators that allow customers to estimate the value of their items before they ever request a mailer. The calculators aren’t just a convenience. They’re an extension of our belief that uncertainty shouldn’t be part of the buying process.

Transparency often makes individual transactions harder. Customers ask more questions. They negotiate more. Some decide not to sell at all. But over time, transparency makes the business easier because customers stop wondering what you’re hiding. When people trust the process, every conversation starts from a stronger foundation.

Systems over discretion

Instead of leaving evaluations open to individual interpretation, we standardized them so outcomes wouldn’t depend on who happened to answer a customer’s call that day. Every offer is based on the same defined criteria rather than personal discretion. Standardizing the process reflected the kind of company we wanted to build. Customers shouldn’t have to wonder whether they’d receive a different offer if they spoke to someone else.

Consistency gives people confidence that they’re being treated fairly, regardless of who they interact with. The goal wasn’t to eliminate judgment. It was to make sure every decision reflected the same standards. When fairness isn’t left to individual judgment, trust grows.

Operational rigor over speed

Early on, we resisted the temptation to grow faster than our systems could support. Like many startups, we felt pressure to move quickly, expand and scale. But we also knew that every operational weakness would become more visible as the business grew. Scaling inconsistent experiences only magnifies problems.

Instead, we invested time in refining our processes, documenting clear standards and building systems that could deliver the same level of service every time. Those investments weren’t always visible to customers, but they shaped every interaction they had with us.

Growing quickly is exciting. Growing consistently is much harder. We learned early that every shortcut becomes more expensive as a company scales. Investing in strong systems upfront wasn’t always the fastest path, but it meant we could grow without asking customers to absorb the cost of our growing pains.

That isn’t just our experience. Research from PwC similarly argues that trust isn’t owned by marketing. It’s created through leadership decisions, operational discipline and accountability across the organization.

We designed every interaction assuming customers were comparing us to the worst experience they’d ever had, not our closest competitor. That mindset helped to frame everything, from how we communicated expectations to how we handled questions and difficult conversations. Every decision was filtered through a simple question: Does this make the customer feel more informed, more respected and more confident?

It’s simple to optimize a business for transactions. It’s much more difficult to optimize for trust. We believed that creating a better experience wouldn’t just improve a single sale; it would create repeat customers, referrals and a reputation that competitors couldn’t easily replicate.

Visibility over plausible deniability

We quickly learned that leadership should never be insulated from operational mistakes. It was important to us that if customers experience friction, leaders should feel it too. It’s easy to build layers that shield executives from day-to-day problems, but every layer of distance makes it harder to understand what customers are actually experiencing. 

We made it a priority to stay close to customer feedback, because operational blind spots don’t disappear on their own. They grow. When leaders have visibility into what’s working and what isn’t, accountability becomes part of the culture rather than a response to a crisis. 

Transparency leaves leaders with fewer places to hide, and that’s exactly the point.

Trust is the only moat that gets stronger when shared

Technology eventually catches up. Prices get matched. Features become commodities, and even today’s AI advantage will narrow as competitors adopt the same tools. Most competitive advantages have a shelf life.

Trust behaves differently. The more consistently a company earns it, the more valuable it becomes. Competitors can copy products, pricing models and even customer experiences, but they can’t instantly replicate the culture, operational discipline and leadership decisions that created years of credibility.

PayPal is a good example. It didn’t invent online payments. It helped make them mainstream by reducing perceived risk through buyer protection, fraud prevention and greater transparency around digital transactions. The technology mattered, but widespread adoption happened because people trusted the experience.

The same principle applies across industries. Customers don’t simply adopt new products because they’re available. They adopt them when they believe the company behind them has earned their confidence.

By the time trust becomes part of your reputation, it’s already the product of countless decisions your competitors can’t easily see or recreate.

The takeaway

Every founder wants a moat. While most look outward, the strongest ones build inward.

It’s easy to believe the next advantage will come from a new feature, a lower price or the latest technology. Those things matter, but they’re rarely what customers remember. They remember whether your company delivered on its promises. They remember whether the process felt fair. Most of all, they remember whether they believed you.

Leadership isn’t about building systems that maximize advantage over customers. It’s about building organizations that deserve their confidence. Every decision, from how you communicate to how you respond when something goes wrong, either reinforces or erodes trust. That’s the kind of moat no competitor can replicate overnight.

In a world where nearly everything can be copied, trust remains one of the few competitive advantages that still has to be earned.

Every founder wants a moat. We spend countless hours discussing product differentiation, defensibility, AI, proprietary data and network effects. But after spending the last several years building a company in one of America’s least trusted, most opaque industries, I’ve come to believe we’ve been asking the wrong question. The most durable competitive advantage isn’t what you build. It’s whether customers believe you. 

In industries where customers feel confused, skeptical or taken advantage of, trust becomes the moat. But trust isn’t built through slogans or advertising. It’s built through operational decisions that customers experience every day. Unlike most competitive advantages, trust compounds. 

Why opaque industries create the greatest leadership test

Many industries remain opaque, not because they are inherently complicated, but because opacity has historically been profitable. Complexity creates leverage. If customers don’t understand how something works, they can’t easily compare offers, evaluate fairness or recognize hidden costs. Confusion does the heavy lifting. Businesses no longer have to earn trust because complexity protects them from scrutiny. That’s when companies begin optimizing for information asymmetry, margin extraction, low accountability and short-term transactions instead of long-term relationships. 

Some of the best investment decisions I’ve made never show up anywhere. No press release. No board seat. No update email celebrating traction. Just a quiet “no” on something that, in the moment, felt very close to a “yes.”

That’s the part of investing that doesn’t get talked about enough. The discipline to walk away when everything in the room is leaning forward. When the founder is convincing, the idea is compelling and the momentum starts to build in a way that makes hesitation feel like a mistake.

After years of investing in early-stage companies, sitting through countless pitches and working closely with founders at every stage, one thing becomes clear: Attractive opportunities carry their own kind of risk. Sometimes more.

Here are three kinds of deals I walk away from, and why.

1. A great product with the wrong cost structure

One of the more interesting ideas I came across was a rapid hydration test for athletes. It was clever, easy to understand and had real consumer appeal. You could picture it on shelves. You could imagine the branding. It checked a lot of boxes very quickly. Then you started to peel it back. What did it take to manufacture at scale? What did distribution look like? How much capital was required just to get to a point where the market could even react? The answers weren’t easy (or cheap).

I’ve seen this pattern enough to know how it plays out. The idea gets attention, maybe even early excitement, but the business underneath it demands constant funding just to stay alive long enough to prove anything. That kind of pressure compounds quickly. It narrows your margin for error to almost nothing.

A similar situation came up with a custom furniture concept built around CNC technology. The output was impressive. High-quality, scalable in theory, differentiated from traditional manufacturing. But the financial engine behind it required heavy upfront investment, operational precision, and time. A lot of time.

In both cases, the product worked on paper. The economics created a different story. Risk doesn’t always sit in the idea. Sometimes it’s buried in what it takes to make the idea real.

2. A founder you want to believe, but can’t fully back

You meet a founder who is charismatic, driven and absolutely convinced they are onto something big. They communicate well. They create energy in the room. They sell the vision in a way that makes you want to lean in. And then something feels off. I’ve learned to pay attention to that.

One founder I met was building a business tied to a major social platform. The concept made sense. The timing felt right. The delivery, though confident, came across as “off” to me. He tipped over into abrasiveness; his answers may have been right for all I know, but they had an edge. And when he started asking me for introductions, I wasn’t ready to have my name tied to his. Regardless of the idea, I don’t want to be in business with people like this.

Then there are the one-dimensional founders. The brilliant scientist with a breakthrough idea but no grasp of how to build a company around it. The operator who understands execution but is stepping into a technical space without the depth to navigate it. Both scenarios create gaps that are hard to close under pressure.

In one case, I looked at a healthcare concept involving at-home testing. Interesting model, real potential, completely outside my lane. That alone became a deciding factor. If I can’t understand the underlying risk, I have no business pretending I can manage it.

There are also smaller signals that tend to show up early. A founder hiring a COO before a product even exists. Loose thinking around expenses. A financial plan that feels more like a placeholder than a strategy. Individually, these things might seem manageable. Together, they paint a picture.

First-time founders absolutely can and do succeed. Some build extraordinary companies. But experience leaves marks, and those marks matter. Founders who have been through failure often carry a different level of awareness, a sharper sense of what can go wrong and how quickly things can unravel. In early-stage investing, you are not just backing an idea. You are underwriting a person’s judgment.

3. A strong concept entering an unforgiving market

Some opportunities check every box you expect: a clear product, a capable founder, a clean pitch and early signs of traction. You walk into the meeting expecting to find something wrong, only to find something that holds together. Then you look at the market.

I spent time with several founders in the skincare space who had built thoughtful, well-positioned products with good branding and a clear audience. They had a solid understanding of what they were trying to do. But they were stepping into a category dominated by companies with massive R&D budgets, global distribution and deep customer loyalty. The kind of incumbents that don’t just compete; they absorb. Breaking through in that environment requires more than a good product. It requires a level of differentiation and staying power that can withstand sustained pressure from players who operate at a completely different scale.

That’s where the risk lives. Your product might work; it might be the best skin care product ever conceived, but it might still have no real path to visibility, adoption and longevity once it hits the market. Saturation has a way of compressing outcomes. It turns good ideas into background noise.

The discipline behind the decision

Walking away from these deals wasn’t about finding obvious flaws. Each one had elements that could have worked. That’s what makes these decisions difficult. You’re not rejecting failure. You’re passing on potential, and that’s where discipline comes in.

Founders are wired to sell a vision. Sometimes that vision stretches far beyond what’s realistic in the near term. That’s part of the role. They have to believe. They have to push. The investor’s role is different. You can trust the founder. You can respect the ambition. You can even believe the idea has merit and still decide the risk profile doesn’t align.

Over time, you realize momentum in the room doesn’t translate to durability in the business and excitement has the ability to amplify risk. The longer you stay in this world, the more you understand that saying no is the difference between staying in the game and chasing something that was never going to get there.

Some of the best investment decisions I’ve made never show up anywhere. No press release. No board seat. No update email celebrating traction. Just a quiet “no” on something that, in the moment, felt very close to a “yes.”

That’s the part of investing that doesn’t get talked about enough. The discipline to walk away when everything in the room is leaning forward. When the founder is convincing, the idea is compelling and the momentum starts to build in a way that makes hesitation feel like a mistake.

After years of investing in early-stage companies, sitting through countless pitches and working closely with founders at every stage, one thing becomes clear: Attractive opportunities carry their own kind of risk. Sometimes more.

I first saw the hotel Castelfalfi from the back of a cab, its stone exterior rising out of the Tuscan hills. Inside waited founders who collectively generate more in annual revenue than some small countries — and each had paid thousands of dollars for the privilege of being there.

On paper, I had no business being at a $14,000 retreat for seven- to nine‑figure founders in Tuscany. I don’t run a massive consumer goods brand or a unicorn startup, and my net worth is far from impressive. But when I was invited to sit in on three days of keynote sessions and fireside chats at the OOAK Mastermind conference, I couldn’t turn down the chance to see what happens when ultra‑successful founders gather behind closed doors.

OOAK Mastermind was hosted by OOAK, short for One Of a Kind. The global consumer brand-building company creates, scales and acquires brands.

The three co-founders of OOAK were everywhere at this event. Bob Verlaat, Nick Nijhof and Vince Nijhof delivered the keynotes and moderated the fireside chats. The three of them are actually best friends from childhood; Nick and Vince are brothers.

The three founders came up with the idea for this event after hosting two smaller iterations in Dubai. They originally intended to keep this conference small, with only a few dozen participants, but kept attracting more interest and selling out.

What surprised me most was how young everyone was. Vince, Nick and Verlaat are all under 30 years old, and they were able to attract an audience of about 100 young founders.

The experience 

The event was at the Castelfalfi resort in the heart of Tuscany, Italy. The village of Castelfalfi was a five-minute walk from the hotel and featured a row of shops ranging from a clothing store to a gelato shop. Everywhere I looked, there were scenic views. 

Event participants paid $14,000 for five-star accommodations, meals and airport transfers. Attendees had to apply and have a proven track record of leading a seven- to nine-figure brand.

Besides the three OOAK founders, speakers at the event included Jeff Srithongrung, director of creative strategy at TubeScience, and Ray Jang, founder and CEO at AI ad company Atria. Srithongrung spoke about how to run an effective ad campaign and the benefits of changing an ad to appeal to different audiences. Jang spoke about the transformative effect of AI in advertising and said that AI has reduced the cost of testing concepts and trying new things to “close to zero.”

On Saturday afternoon, I joined the conference participants for a truffle-filled lunch: We had beef tartare with truffle as a starter, truffle risotto for the main course and vanilla truffle mousse for dessert. I sat with founders working on selling everything from supplements to gold. 

One attendee spoke about his success

Most event participants were brand founders. One speaker, 32-year-old Alvaro Gellings, revealed that he built an apparel brand and sold $1.4 million worth of products within the first hour of launch. He then built a sportswear brand called Day One and tapped into a partnership with German creator and endurance athlete Arda Saatçi. Gellings, who was also an attendee at the conference, knew that selling sportswear required more than just having a quality product. 

“Nobody’s looking for the next gym tank to buy,” he says. “Nobody’s in urgent need of the next T-shirt, the next socks, the next shoes. You have to create a story.”

Gellings created a highly publicized story: Saatçi would run 1,960 miles from Berlin to New York. 

He would start in Berlin and run across Europe to Porto, Portugal, then take a flight from Porto to Boston. For the final stretch, he would run from Boston to New York. He would do it all while wearing Day One sportswear, and the company’s official launch would be tied to him completing his run.

It took Saatçi 74 days in 2024 to complete the task. The ad campaign had “everyone posting,” Gellings says. It was a prime example of how companies can leverage partnerships with influencers to make their brands more recognizable and focus on the story, not the product. 

Framing products in new ways

The OOAK co-founders hosted a number of talks at the retreat, and I sat down with the trio before the event started to hear more about their entrepreneurial journeys.

Even if you don’t know OOAK, you may recognize one of their portfolio brands, like earplug company Hears and sleepwear startup Dore & Rose. Verlaat, Nick and Vince founded Dore & Rose in 2022, followed by Hears in 2023 and subsequently grouped the businesses under the holding company OOAK.

Verlaat oversees brand, creative direction and positioning while Nick handles product and people and Vince focuses on growth, paid acquisition and supply chain execution. 

“We all had a very separate skill set [when we started], and we still have [that],” Verlaat says.

He added that his blueprint for launching brands, his core thesis, was to take a “boring” product and frame it differently. For example, the founders position Dore & Rose as a premium sleep-wellness brand rather than a conventional bedding retailer, selling mulberry-silk sleep products infused with silver ions. They emphasize overnight skin recovery and restorative sleep.

The founders took a relatively familiar product, the silk pillowcase, and pushed it toward an emotionally richer category: beauty, wellness and sleep quality. It’s a silk pillowcase brand positioned as beauty, not bedding. 

Hears applies the same playbook to hearing protection: It sells earplugs for music, nightlife and event environments but positions them as a premium lifestyle product rather than a mere accessory. Its public narrative is about enjoying music clearly and confidently while protecting hearing. The founders repositioned the earplugs as a fashion product, not a medical device.

The outcome

So far, the way they market their products is paying off: The founders disclosed that OOAK Brands is making a combined yearly revenue of $100 million. They are targeting $200 million this year. 

In addition, they have sold over one million silk items through Dore & Rose and have placed their silk products in 50 five-star hotels, like Four Seasons, Belmond and Cheval Blanc. Dore & Rose has partnerships with over 150 retailers, including Nordstrom, Mecca and Namshi.

Meanwhile, Hears hit $7 million in revenue in its first year, 2024. Since then, the brand has sold more than 250,000 pairs of earplugs. Hears partnered with the Hearing Health Foundation to donate a portion of revenue and raise awareness for hearing protection. 

Their advice

Verlaat’s advice for potential founders waiting to make the leap is to “just do it.” “What’s the worst thing that could happen, really?” he says. “You don’t die.” 

He says that he knew from the start that he would succeed. “We always believed that we’re going to get to where we are today.”

Vince pursued entrepreneurship because he “wanted to work and make money.”

“I wanted to just go harder,” he says. “For me, I think I figured out really, really soon that working for a boss was not going to cut it for me.”

Nick was candid that founders needed to “wear multiple hats,” especially in the early stages of building a business. He is also an advocate of just getting started, even if a founder doesn’t have everything figured out. “You don’t need to see the finish line. You don’t need to know where it will end,” he says. “As long as you know your next step, eventually you will get there.”

I first saw the hotel Castelfalfi from the back of a cab, its stone exterior rising out of the Tuscan hills. Inside waited founders who collectively generate more in annual revenue than some small countries — and each had paid thousands of dollars for the privilege of being there.

On paper, I had no business being at a $14,000 retreat for seven- to nine‑figure founders in Tuscany. I don’t run a massive consumer goods brand or a unicorn startup, and my net worth is far from impressive. But when I was invited to sit in on three days of keynote sessions and fireside chats at the OOAK Mastermind conference, I couldn’t turn down the chance to see what happens when ultra‑successful founders gather behind closed doors.

OOAK Mastermind was hosted by OOAK, short for One Of a Kind. The global consumer brand-building company creates, scales and acquires brands.

From movies to novels, we’ve been told that a business sprouts best in the most fertile garden. In The Social Network, Mark Zuckerberg drops out of Harvard and heads west to grow Facebook in the new tech hub of Palo Alto. The Great Gatsby finds rural North Dakota boy James Gatz moving to Long Island to build his business and reinvent himself in the process.

These may be works of fiction, but in real life the startup guide has been the same for decades. If you wanted to launch a successful business, you went where the opportunity was. In this vein, Silicon Valley became synonymous with innovation. New York dominated finance and media. Boston excelled in biotechnology, and so on.

Today, that assumption is extinct. AI, cloud computing and the adoption of remote work have changed the dynamics of starting a business. Founders no longer need to be in a major civic hub to access trained talent, sophisticated business tools or even global markets. Aspiring founders are now choosing where to build companies based on affordability, operating costs and lifestyle.

More than 548,000 new U.S. business formations took place this past June, the strongest June on record, and nearly 3.5 million through the first half of the year. But the interesting trend is where many of those businesses are launching. States like Oregon, Mississippi and North Dakota posted some of the nation’s strongest year-over-year growth, while Wyoming remains a magnet for new business formations, especially LLCs and out-of-state ventures. These hotspots underscore that entrepreneurial momentum is becoming more geographically diverse.

AI changes the economics of company building 

Until just a few years ago in the pre-ChatGPT world, launching a startup usually required hiring employees or outsourcing work. Entrepreneurs needed analysts to conduct market research, programmers to develop websites, designers to create marketing materials, writers to produce content and customer service reps to serve as liaisons. Now AI allows founders, even solo or two-person ventures, to perform many tasks themselves before making their first hires.

Let’s be clear: This doesn’t replace expertise or eliminate the value of seasoned employees, but it does significantly lower the cost and complexity of going to market. This means that one of the strongest advantages of traditional startup ecosystems – access to large pools of talent and cash – is no longer essential to nurture a company through its earliest stages.

Remote work unchains employees from offices

Along with powerful AI tools, post-COVID remote work has altered another enduring business assumption: that employers and employees must share the same offices. Many founders now recruit nationally or globally, customizing their teams based on expertise rather than ZIP codes. Software developers can work in Colorado, designers in North Carolina, accountants in Texas. Meanwhile, a company’s leaders can operate somewhere else, nearly anywhere they’d like.

This flexibility gives entrepreneurs something previous generations rarely had: the freedom to choose where they want to live without impeding access to talent. Instead of asking themselves, “Where do I need to move to build my company?” founders now ask, “Where can my company give me a strategic advantage?” and “Where do I want to operate from?”

Geography still matters for different reasons

As they say in real estate, it’s still about “location, location, location.” Geography continues to matter in many ways, but not because of specialized business hubs.

Lower commercial rents reduce overhead. Business-friendly tax policies improve cash flow. Decreased housing costs benefit founders and staff alike. Shorter commutes and better access to bike lanes and outdoor recreation can improve quality of life and help prevent burnout amid the nascent years of company building.

For entrepreneurs bootstrapping a business, every dollar they can save on overhead is a dollar that can be invested in product/service development, hiring or customer acquisition. Cities don’t have an irresistible magnetic pull anymore because they’re the preeminent hub for tech, finance or anything else. Unless your vision is a location-based business like a restaurant, retail shop or amusement park, more and more founders are unshackled by a “required” location.

Build where you can thrive

Business formation data suggests that the redistribution of entrepreneurship is accelerating. Communities that historically struggled to attract startups now find themselves competing on strengths that matter to today’s entrepreneurs: affordability, broadband connectivity, favorable tax climates and a high quality (and often slower pace) of life.

Wealth creation is becoming increasingly democratized, pushing into previously overlooked parts of America with a surge in LLC formations. Today, successful companies are as likely to emerge from midsize cities, suburban communities or even rural regions as from traditional metropolitan corridors.

Entrepreneurs have always been encouraged to “Think differently.” With a leg up from AI and remote work, that mindset is extending into where they plan.

From movies to novels, we’ve been told that a business sprouts best in the most fertile garden. In The Social Network, Mark Zuckerberg drops out of Harvard and heads west to grow Facebook in the new tech hub of Palo Alto. The Great Gatsby finds rural North Dakota boy James Gatz moving to Long Island to build his business and reinvent himself in the process.

These may be works of fiction, but in real life the startup guide has been the same for decades. If you wanted to launch a successful business, you went where the opportunity was. In this vein, Silicon Valley became synonymous with innovation. New York dominated finance and media. Boston excelled in biotechnology, and so on.

Today, that assumption is extinct. AI, cloud computing and the adoption of remote work have changed the dynamics of starting a business. Founders no longer need to be in a major civic hub to access trained talent, sophisticated business tools or even global markets. Aspiring founders are now choosing where to build companies based on affordability, operating costs and lifestyle.

Some of the hallmarks of a successful entrepreneur include the ability to self-actualize through rigorous study, continuous learning, relentless tenacity and the resilience to rebound after setbacks. 

I know this firsthand. At 25, my goals were set in stone. I knew what I wanted: a career in architecture. At the time, I was enrolled in UCLA’s master’s program in architecture, studying and working on projects nonstop, setting the bar as high as I could. The renowned Pritzker Prize-winning architect Thom Mayne was my mentor. I was at the top of my game.  

Then, overnight, I received the blow of a lifetime: I was diagnosed with a brain tumor that required immediate surgical intervention. When I awoke, staring at the cold, clinical hospital ceiling, I had 150 stitches on the side of my head and was unable to move. However, I was able to discern two searing sentences of a conversation between my mother and the surgeon. 

“What have you done to my son?” My mother railed at the doctor. 

“I have given him 50 more years of life,” the doctor replied decisively. 

From that moment on, I knew I had to make that 50-year gift count. After taking half a year off from my studies, I returned to class with renewed zeal — and mounds of debt. Despite the appearance of gradual recovery, I had a long road ahead. 

Still, I was determined to make the most of every moment. But the medical bills kept piling up, and I was forced to make a drastic change — a pivot to a high-income skill. While searching online, I found day trading, which I understood less than nothing — but not for long. I studied the discipline for countless hours, delving into books, podcasts and YouTube videos until my brain hurt. I became so assiduous and single-minded that I knew I had to go further and immerse myself completely in my new focus. 

By sheer force of will and necessity, I absented myself from everything and everyone I knew. My colleagues and friends thought I had taken leave of my senses. My family didn’t know what had become of me. I sold my car, changed my number and ensconced myself in an office in an LA skyscraper for $230/month. 

“What happened to David?” echoed faintly in my ears, carried by the grapevine. But I didn’t care what anyone thought. I had “burned the boats,” as Hernán Cortés told the Conquistadors in the 16^th century. There was no turning back. I had survived life-altering surgery; now my future was on the line, and I had to shape and claim it. 

To support my new venture, I took on odd jobs as a tutor and an Uber driver. The landlord kept knocking on my door, and the creditors couldn’t wait. While these practicalities held sway, I worked day and night, sleeping on the floor of my office to ensure wakefulness at the market open.  

In my personal life, I became a minimalist — again, not by choice, but by necessity. For example, when the world went into lockdown during the Covid-19 pandemic, all the gyms were closed, and I had nowhere to shower. So, I resorted to Skid Row. Stoic and poker-faced, I walked through the streets of downtown L.A., intent on reaching my destination undisturbed. I had 10 minutes to shower and then return to monitor my trades. Everything was the trade. 

When I wasn’t trading, I read voraciously and studied into the night, honing my skills, journaling and envisioning. The Law of Attraction was central to my approach. I truly believed — as I still do — that what I projected in my mind’s eye would manifest. And so it did: I became a high-stakes, 7-figure day trader with a 90%-win rate.  

However, success was not an overnight phenomenon. It required rigorous discipline and sacrifice. Some might say my tactics were extreme, but I had no choice. I had to become an autodidact, front-loading all my strategies and literally devising them. The result was a set of proprietary winning strategies that I share in my book, Short Selling Master: Proven Strategies from a High-Stakes Day Trader (Harriman House). 

My objective: to vanquish the 96% failure rate in my industry by providing cogent strategies for success. Today, I have become the mentor I never had, with the opportunity to witness others advance in the field and attain financial freedom.

Some might say that my unique methodology for attaining success — a compelled absence from mainstream society — was extreme. Indeed, that plan took all the fortitude I could muster. In no guise do I advocate such a plan for my students or other aspiring traders. But looking back, I have absolutely no regrets. Hard work and ingenuity led me to where I am today. I hearken back in gratitude while moving forward and lifting others up.  

Some of the hallmarks of a successful entrepreneur include the ability to self-actualize through rigorous study, continuous learning, relentless tenacity and the resilience to rebound after setbacks. 

I know this firsthand. At 25, my goals were set in stone. I knew what I wanted: a career in architecture. At the time, I was enrolled in UCLA’s master’s program in architecture, studying and working on projects nonstop, setting the bar as high as I could. The renowned Pritzker Prize-winning architect Thom Mayne was my mentor. I was at the top of my game.  

Then, overnight, I received the blow of a lifetime: I was diagnosed with a brain tumor that required immediate surgical intervention. When I awoke, staring at the cold, clinical hospital ceiling, I had 150 stitches on the side of my head and was unable to move. However, I was able to discern two searing sentences of a conversation between my mother and the surgeon.