Here it is in order, from a camera in college to the work I do now. The failures did more for me than the wins.
College
San Diego, CA
San Diego State
My first business was a camera and an SEO strategy.
I started a small business in college offering photography services to sorority girls who wanted to do a calendar. How could I say no?
Then a friend taught me SEO back in 2010, and I used it to expand into different service lines and build the largest photography school in San Diego. Most photographers love photography. I figured out pretty fast that I was more in love with building and scaling businesses, so I sold the school and the service company and went to build a tech company.
BootstrappedProfitable
Next
First tech startup
Togally
Togally, a marketplace to hire photographers.
We had a killer product, customers, and growth. We also spent more time pitching investors than acquiring customers, and it didn't work. Then we chased a weak acquisition offer from Kodak that never materialized.
These are the mistakes I now watch founders make every week, and the ones I help them avoid before it's too late.
Customer acquisition beats investor pitching
$12M raised, an acquisition that died at 2am, then a sale to Walmart.
LiquidSky was a cloud gaming technology company that solved a big problem. We built a GPU edge compute network that let gamers play any game on any device, and we raised $12 million, with Samsung as one of our largest investors.
We spent six months in due diligence with Samsung to acquire the company. Then on closing day, during business hours in Korea, we got a text message that the deal was dead. The CEO of Samsung had gone to prison for political corruption.
Navigating that news with no cash, pissed investors and confused employees is what shaped me into the leader I am today. We turned the company around and sold it to Walmart at the end of 2018, which was a massive success.
Raised $12MDeal died at closePivoted to B2BAcquired Dec 2018
2019 to 2021
President & COO
Generation Esports
An $11M Series A and a pivot in the middle of a pandemic.
Generation Esports was doing $100K a year when I joined, after seven years of operations. I took them to a $6M run rate in 18 months, reaching 100,000 students across 3,000 schools in the US. It was one of the most rewarding experiences of my career. I took the team from 7 guys living on ramen and passion to raising $11M and scaling to 65 people.
All while navigating a pandemic where most edtech companies collapsed. I thrive in chaos, especially those very complex, convoluted situations. In times like those, I can get everyone on track towards one goal.
Series A · $11MPivoted through COVID
2020
New York · New Jersey · London
Angel + LP
Four exits in, I started writing checks.
Since 2020 I've been writing checks into startups, which is a common mistake most exited founders make. I made a lot of bad bets.
I've learned to focus on building relationships with proven entrepreneurs instead of being a passive small check writer. My checks don't mean a lot. My experience and contribution have transformed businesses and founders.
Angel investorLP in multiple funds
Thunder, the podcast, and ExitBoard are all the same job.
Seeing founders make avoidable mistakes at the early stages, and again when they're about to transact, is what led me to the work I do today. I started interviewing the founders and investors who made it through, because their answers were better than any framework.
ExitBoard is where those answers live now, so a founder at 11pm on a Sunday can get several real points of view and form their own opinion, instead of waiting on one banker's advice.
I spend my days supporting founders, helping them navigate their most challenging moments with their businesses to achieve their ideal outcome of a transaction.