I’ve spent my career straddling the line between founder and investor.
I’ve launched eight companies, taken three from idea to exit, and backed dozens of early-stage teams.
Along the way, I’ve learned that trust and alignment matter more than spreadsheets or slide decks—especially when markets get shaky.
Table of Contents
The Volume Game: Reality of Early-Stage Investing
One truth that aspiring investors often miss is the sheer volume required for success.
About 90% of the businesses you invest in will fail – that’s just the nature of the game. If you’re only writing one check every few months, you’re not playing the odds correctly.
“I invest in one company every once in a while” is a mindset destined for disappointment. If you genuinely want investment returns, you need to be writing about ten checks annually.
There are certainly people who invest for social status or networking opportunities, but if making money is your goal, volume is non-negotiable.
This reality creates both a challenge and an opportunity. You need sufficient capital to maintain this pace, and you must accept that most ventures won’t succeed – regardless of how convincing the founders are during their pitch.
Why I Put My Own Capital on the Line
A cornerstone of my investment philosophy is using only my own capital. I choose not to invest other people’s money, which fundamentally changes my relationship with founders in a way that creates genuine alignment.
Putting personal money into every deal keeps me honest. The founders know I’m not managing someone else’s expectations or chasing artificial multiples—I’m shoulder-to-shoulder with them.
Because my returns aren’t tied to a venture fund’s timeline, I’m comfortable supporting an exit that triples our money in two years instead of swinging for a mythical 100X return that might never materialize.
By investing my own funds, our incentives are directly synchronized.
We’ve had multiple businesses we’ve invested in that have sold, and while they might not have been considered “venture scale” exits, we tripled our money in a year or two.
That’s a fantastic outcome that makes everyone happy. I don’t need every investment to be a home run; consistent wins compound over time.
Trust: The Hidden Multiplier in Founder-Investor Relationships
Term sheets outline equity; trust determines outcomes. The traditional venture model often creates problematic situations where misalignment leads to poor decisions.
When founders and investors trust each other, they make better choices that benefit everyone involved.
Embracing Founder-Friendly Capital
I’ve seen scenarios where founders receive acquisition offers that would be life-changing personally – enough money to be set for life. But their investors, who need outsized returns to make their fund economics work, push them to continue growing.
This frequently leads to companies becoming too valuable to be acquired yet still unprofitable. Eventually, they sell at a significant discount.
After preferences are paid to investors, founders who spent a decade building may walk away with surprisingly little – sometimes less than they would have earned at a steady job.
By removing these pressures, I can have honest conversations about what’s genuinely best for both the company and the founder.
Taking venture money often means those investors need a certain outcome because they’re investing other people’s money, which comes with expectations for specific high returns.
My approach of investing personal capital sidesteps much of this pressure.
Looking for Grit: Betting on People, Not Plans
I back people who combine stubborn optimism with raw grit—founders who’ll absorb a string of ‘no’s, pivot when reality demands, and come back swinging the next morning.
The original business model that anyone pitches is almost never what they end up doing, so it makes little sense to overanalyze the initial business plan.
A perfect example is a friend who founded one of the most valuable AI companies in America.
Her early investors didn’t back her because they foresaw the AI revolution – they invested in an app for skipping nightclub lines.
The business pivoted dramatically before finding its true path to success.
This is why I focus more on the founder than the idea. Can they handle constant rejection?
Can they show up day after day when things look miserable? Do they genuinely want to keep going despite all the challenges? That resilience is what I’m betting on.
The Founder’s Mindset: Strategic Naivety
Interestingly, my approach as a founder is almost the opposite of my investor mindset.
When starting companies, I’ve found value in embracing a certain amount of strategic naivety.
As a founder, I want to maintain blind optimism that something is going to work. I often prefer entering industries where I don’t have extensive prior experience.
This helps me avoid the trap of knowing too much about the challenges ahead.
When you know too much about an industry, you might never start because you’re already aware of all the obstacles and reasons something “can’t be done.”
Looking back at many of my businesses, if I had known in advance how difficult they would be, I might never have started.
That naivety served me well – it forced me to figure things out as I went along, without being limited by conventional thinking.
Turning Volatility into Opportunity
Economic downturns scare off capital—and that’s exactly when the best vintages get bottled.
I’ve discovered that periods when most people avoid investing often present the best opportunities.
While many investors freeze their checkbooks during uncertainty, I look for founders still shipping products and winning customers.
Valuations become more reasonable, competition thins out, and the eventual upswing rewards those who kept building.
My role is to stay calm, provide runway, and remind the team that uncertainty is fuel for creativity, not a stop sign.
It’s similar to the stock market – when it’s in free fall, those who remain calm and have cash available often find the most advantageous entry points.
Institutional investors typically slow down during uncertain times because their limited partners get nervous about deploying capital during “uncertain” periods.
In retrospect, many of today’s most important companies secured funding during economic downturns when capital was scarce.
The companies that survive these challenging environments often demonstrate the kind of resilience that leads to extraordinary outcomes.
Keeping Dry Powder: Balancing Patience with Liquidity
Early-stage investing demands both volume and stamina.
I write enough checks each year to let the power-law work, but I also pause periodically to ensure the portfolio’s paper gains have a path to liquidity.
After actively investing for several years, you might have a portfolio that looks fantastic on paper, but if nothing is liquid, you naturally question how long things will take and if those investments will truly pan out.
These periods of reassessment are healthy. They force you to evaluate whether your strategy is working and when you might actually see returns rather than just paper gains.
Cash reserves give me the confidence to double down when a standout company pivots into its breakout moment—like Bluon transforming from a refrigerant replacement into the data backbone for 60% of America’s HVAC technicians.
This company began as a replacement for a chemical being phased out, but through insight and evolution, it became one of the largest data companies in the HVAC industry.
It’s been incredibly rewarding to watch that pivot from a physical product into a technology powerhouse.
Knowing When the Time is Right
Timing is everything. One of the hardest skills to develop is knowing when to sell a business – whether as a founder or an investor.
For me, the decision has never been purely financial. I ask myself: Am I still energized by the problems this business presents? Different stages of growth require different skills and interests.
The challenges of early customer acquisition are vastly different from managing large teams or creating five-year forecasts.
I’ve learned to be honest about whether I’m still the right person to lead a company through its next phase. This self-awareness has proven invaluable, both for my own well-being and for the success of the businesses I’ve built.
The Bottom Line
Building valuable companies takes time – often 10-15 years, not months or quarters. Trust, alignment, and disciplined patience serve as my compass when the macro picture turns murky.
I prefer creating sustainable, continuous ways to generate returns and compound wealth rather than chasing unicorns.
By investing my own capital in sufficient volume, focusing on founders with extraordinary grit, aligning our interests authentically, and recognizing that the best opportunities often emerge during the most challenging times, I’ve built an approach that works through all economic cycles – even when the future seems most uncertain.
If you’re a founder navigating uncertainty and looking for an investor who’s equally invested—both financially and emotionally—let’s talk.