I have spent more than fifteen years building companies and buying real estate, and I can tell you the most valuable lesson did not come from a boardroom. It came from paying attention to where other people would not look.
Everyone wants the glamorous deal. The tech launch with the countdown timer. The industry with the magazine covers and the conference keynotes. And because everyone is crowding into the same well-lit room, that room gets very expensive and very crowded. Meanwhile, right next door, there are markets throwing off real cash, run by real operators, that nobody wants to be seen in. That is where I have built most of what I own. That is where I still bet.
This is the honest version of how I think about it.
The opportunity is in the places people are embarrassed to want
Here is a truth that took me a while to say out loud: status-chasing is one of the greatest gifts an investor can receive, because it clears the field.
When capital and talent stampede toward whatever is fashionable, they leave enormous, boring, cash-flowing markets almost completely alone. Cleaning. Property management. Trades like plumbing, electrical, and HVAC. Home services of every kind. These are not small niches. They are the operational backbone of how people actually live, and they are deeply fragmented, under-managed, and starving for anyone who will show up and run them well.
Nobody grows up dreaming of owning a cleaning company. That is precisely the point. The unglamorous label is the moat. When an industry cannot confer status, the status-seekers stay away, and the returns stay available for the person who is willing to trade applause for cash flow.
I have never been embarrassed to want a business that works. I would rather own something that quietly pays every month than something that looks impressive at a dinner party and bleeds money underneath the table.
Underestimated founders are the market’s biggest mispricing
If overlooked industries are undervalued, underestimated founders are the deepest inefficiency in the entire market.
The world has a very narrow picture of who a “real” founder is supposed to look like, how they are supposed to talk, what schools they are supposed to have attended, and how much noise they are supposed to make. Anyone who falls outside that picture gets discounted before they open their mouth. Their businesses get passed over. Their capacity gets doubted. Their price, in every sense, gets marked down.
That mispricing is not a tragedy for the investor who can see clearly. It is an edge.
I have watched people run circles around better-funded, better-pedigreed competitors precisely because the world underestimated them for years, and they got very good while nobody was watching. They learned to do more with less because less was all they were handed. They built grit into the foundation because grit was the only material available. When you back a founder like that, you are not doing charity. You are buying a proven operator at a discount the market created out of its own blind spots.
The people others refuse to see are, over and over again, the best investment on the board.
What I actually look for
Conviction is not the same as sentiment. I am warm, but I am not naive. When I look at a founder or a business, I am running a checklist under all the encouragement.
In a founder, I look for four things:
- Grit. Not the highlight-reel kind. The quiet kind, the person who has already survived something hard and did not quit. I want to see how they behave when it is not working, because it will not always be working.
- An ownership mindset. Do they treat the business like it is theirs down to the last dollar, or do they treat problems like someone else’s job? Owners run toward the mess. Employees in their heart run away from it.
- Coachability paired with backbone. I want someone who can take hard feedback without collapsing and without caving. They listen, they adjust, and they still know who they are.
- Honesty about the numbers. The founders I trust most are the ones who tell me the bad news first. Nobody who hides the leak ever fixes the pipe.
In a business, I look for two structural things:
- A fragmented market. Where there are a thousand small players and no dominant operator, there is room to consolidate, professionalize, and win real share. Fragmentation is opportunity wearing work clothes.
- An execution gap. When the demand is obvious but the service is bad everywhere you look, that gap is the whole opportunity. You do not need a miracle. You need to simply do the ordinary things well and consistently, which almost nobody does.
Grit, ownership, fragmentation, execution gap. When those four line up, I lean in, and I lean in hard.
I back people, not just deals
There is a difference between funding a transaction and building a person, and I try never to forget which one I am doing.
A deal is a snapshot. A person is a trajectory. When I invest, I am not just underwriting this quarter’s cash flow, I am asking who this founder will be in five years and whether I want to be standing next to them when they get there. The best returns of my career have come from relationships that compounded, not from clever one-time trades.
That means I invest more than money. I invest access, hard truths, introductions, and the benefit of scar tissue I paid for the expensive way so they do not have to. I have sat across from operators and told them things nobody else in their life was willing to say, because I would rather be the person who tells them early than the polite one who lets them fail.
Building people is slower than flipping deals. It is also the only thing that has ever built anything that lasted.
The specific case for women
Let me be direct about women in business, because I have lived this one personally.
Women get told, in a hundred quiet ways, that certain rooms are not for them. The capital room. The deal room. The room where the real decisions get made. I was told a version of that too. And I want to say something plainly to anyone who has heard it: you do not have to wait for permission to enter the room. You can build the room.
That is what I have done. When I was not handed a seat at an existing table, I built my own tables, my own companies, my own portfolio, and then I made sure there were extra chairs. Being recognized by Utah Business as one of their Women to Watch was meaningful to me, but not because of the title. It mattered because it is proof that the door can be walked through, and that other women are watching to see whether it stays open behind you.
Women founders are, on the whole, one of the most underpriced assets in this economy. They are routinely funded less, doubted more, and scrutinized harder, which means the ones who make it through that gauntlet are, on average, exceptionally capable. The market’s bias against them is exactly what makes backing them so smart. I am not betting on women in spite of the numbers. I am betting on women because the numbers, once you clear away the prejudice, are excellent.
If you are a woman reading this and wondering whether you belong: stop asking the room for a verdict. Go build.
Lifting others as you rise
I hold all of this inside a frame of faith, and I will not pretend otherwise, though I am not here to preach at you.
I believe that what I have been given, the capacity to see value where others miss it, the resources to act on it, the position to open doors, is not mine to hoard. It is mine to steward. Stewardship means the harvest was never only for me. The whole point of climbing is to be tall enough to pull someone else up.
So when I back an overlooked founder, when I invest in a woman building the thing she was told she could not build, when I professionalize an industry everyone else finds beneath them, I do not experience it as a sacrifice of returns. I experience it as the return doing exactly what it was made to do. The cash flow is real, and so is the calling. They have never once been in conflict.
Lifting others as you rise is not a tax on success. In my life it has been the engine of it. The people I have helped up have become partners, referrals, operators, and friends, and the good has compounded in ways no spreadsheet predicted.
That is the whole thesis, said simply. Look where others will not look. Back who others will not back. Build the room, then hold the door. The best opportunities have always been hiding in plain sight, guarded by nothing but other people’s pride.
If this way of seeing resonates with you, I share the unfiltered operator version of it in my newsletter, Operator’s Notes, and I dig into it in longer conversations on my podcast, The Broker’s Table. Come sit down with me. There is a chair here for you.
