My Top 3 Investments and what they have in common

Someone recently asked me about my top investments as an angel investor.

It’s a tough question. Even with nearly 100 checks written, just over a dozen of my portfolio companies have had exits. Some of my “best” potential investments are still growing. Angel investing is a long-term game.

But I don’t judge investments by purely financial measures, either. I invest in visions and founders I believe in. My primary ROI is Relationships Over Investment.

That’s not to say I don’t care about making money. I do, of course. Angel investing is my full time job and I have bills to pay. Financial returns are just one aspect of success I look at.

So when thinking about my top investments, three companies come to mind. They are all trending towards good financial returns, but that’s not why they stand out to me. They are my “top” investments because of their mission and their founders.

I first met Luke Liu when he joined my company Shiftgig a year after he graduated from Northwestern University. He accepted the challenge of wearing many hats, like so many do at an early stage startup. Luke successfully took on multiple projects and was a quick learn.

A year or so later, Luke informed me that he was going to leave; despite my salesmanship, I was unable to persuade him to stay. A week after he left to focus on his startup, I met him for coffee and within an hour, we agreed that I would be the first check in (maybe the 2nd if you include his mom).

The mission was important to me: assisting students with test prep so they could excel in high school and college. Good test preparation could mean the difference between getting a scholarship or not. Luke experienced this problem when preparing for Advanced Placement tests before applying to college. Though the startup was still just an idea, I knew that Luke had the grit to see it through. He even wrote the first test questions and answers himself.

Albert.io has not experience an exit yet but I expect an attractive financial return. However, that is not why this is one of my top investments. The best part of investing in Luke was watching and helping him evolve from a young, uber-talented founder to a seasoned CEO.

It started with raising his angel and venture rounds. I did what I could to open doors and coach him. I was very hands on in the beginning, eventually joining as a board director and weighing in on everything from new hires to GTM strategy.

But as Albert.io grew, Luke did too. He learned to lead, delegate, and manage. The jump from founder to CEO is extremely difficult, but he has done it very well. It has been an absolute joy watching him evolve into the leader he is today.

The Mom Project was founded in 2016 by Allison Robinson, whom I met when I was day-to-day at Shiftgig and a year before I started actively angel investing. Before becoming an entrepreneur, Allison worked as an innovation team leader with the Pampers brand at P&G for several years. When she became a mom herself, she noticed how many women drop out of the workforce after having children. She saw an opportunity to connect women to jobs or gigs that were also compatible with being a parent.

That might sound niche until you realize that ~86% of women will become mothers. That’s nearly 45% of the total population… a massive TAM.

And again, it was a mission I cared about deeply. Allison wanted to build something that made people’s lives better. Since I had experience building a gig marketplace, I knew I could add value. More importantly, Allison and I quickly developed a trusting founder-advisor relationship.

The Mom Project has raised over $100 million to date. My early investment is just a drop in the bucket, but seeing Allison’s vision come to life to serve so many moms and families is a Win.

Finally there is Chowbus, a restaurant-tech platform for Asian restaurants. They started as an Asian food delivery service; while this is a niche food delivery vertical, I personally loved the problem/solution space and wanted to see the co-founders succeed.

As one of the first checks in, I worked closely with Linxin Wen and his team. Linxen and I built a very close relationship. He even referred to me in Mandarin as "Dà gē", or “big brother.”

In the beginning, Linxin and I talked almost every day: product, network effects, growth, financials, team building, culture, and investors. I served on the board of directors for over 6 years from an angel round to seed round to several more venture and growth rounds.

Chowbus experienced incredible growth during the Covid pandemic, but after restaurants opened back up, food delivery demand slowed and competition increased. The founders pivoted to restaurant tech software— a hard pivot from consumer delivery to a B2B restaurant tech.

It is rare for a Series B stage business to make such a dramatic business pivot, but it is working and I credit the determination, tenacity, and grit of the co-founders with the success of this pivot.

Looking at these three investments, there are some clear patterns:

I enjoy being involved in Chapter 1 and helping founders navigate the early days. That’s what makes investing worthwhile to me. It’s not just the financial return. It’s seeing good people and deserving missions win.

I was also asked about my WORST investments ever… but I will save that conversation for another time.