Why I Quit Angel Investing
In 2015 I was frustrated by the arrogance of science in my industry, life sciences, and the lack of appreciation for data and technology, essentially my entire value proposition, and started searching for my next big thing.

Stu, a friend of mine and fellow helictoper pilot, suggested I get into angel investing and introduced me to Sand Hill Angels in April of that year. At the very first meeting when early stage founders pitched to the group of us accredited investors, I knew that I wanted to be a part of it and jumped right in.

I committed to investing a minimum of $25,000 per year and told my husband that I would give it two years and $55,000. I considered it my real life PhD.

In September, I attended my first meetings as a member and went against general angel investing advice by making my first investment into a company called myHealthteam. I was convinced by the CEO Eric Peacock to invest in his company during my very first meeting. After being in life sciences for two decades, I knew that he and his co-founder Mary Ray (and team) were filling a gap and that they were the ones to fill it.

In November, I made my second investment into Sandstone Diagnostics (acquired by Labcorp) and in January 2016, my third into Zum.

By April, I’d invested in TomboyX and realized that my investment thesis revolved around investing in startups that improved people’s lives.

I had quickly joined multiple committees including the life sciences special interest group (SIG), because of my experience in life sciences, and my interest in the space. I went to demo days put on by accelerators and participated in due diligence calls to learn as much as I could, as quickly as possible.

I wanted to be an educated investor and there’s really no way to learn how to be a good angel investor other than to do it. I listened to podcasts and read anything I could get my hands on.

In becoming a good angel investor, the learning curve is steep and there are a lot of variables.

By July 2016, I was on the Board of Sand Hill Angels and quickly exceeded my $55,000 budget. I’d doubled down on two of my investments in addition to making a few new investments. At the time, my average check size was $10,000.

I also realized that most of the angel investors and VC’s were men. I was often one of the only women in the room, with many people assuming I was someone’s wife or one of the staff. Only when I told them I was a commercially rated helicopter pilot did I get their attention. My table stakes as a woman investor (over the age of 40) were too high.

By August 2017, after a year on the Board, I realized that Sand Hill Angels was not for me. There was a serious misalignment of values between how I wanted to operate as an investor and the behavior of others in the group. In retrospect, it was an abusive experience.

I also realized that as a woman investor, I was expected to build the ecosystem to make it friendler to the non-cis-het-white men who made up the majority of the investors. These investors were making the decisions on what got funded, and therefore had too much control over what existed for the rest of us in society. They still do.

So I became vocal. I launched a podcast called Piloting Your Life to show what was possible to those who needed to see it, to be it.

I challenged event organizers on making events more women friendly, having more women on stage to provide different perspectives, and checked men’s (and white women’s) privilege.

The podcast quickly evolved into a season on women investors, women founders who had raised Series A and beyond, and others who supported the ecosystem. I wanted more women to become investors so we could influence what got funded.

95% of the world was designed by and for men and it was time we had our say.

During my first two years, I operated as an angel investor between 30–50 hours a week. I would attend multiple events in a day, review hundreds of pitch decks, research, make introductions, and give feedback on pitch presentations. I even wrote an article on what I looked for in a pitch.

My men investor colleagues sent me the startups with women founders without considering them for investment or offering them assistance.

Women founders expected that I would work with them, for free, to help them get funding and if I said no, they told me I didn’t support women.

It was exhausting, relentless, and for the most part, thankless. I got burned out and I still haven’t fully recovered.

I gave away far too much of my time in a way that my men counterparts weren’t expected to. I knew I wasn’t the only woman experiencing this and in 2019, I wrote a blog post called There Has to Be a Better Way: Changing the World as a Female Investor.

After leaving Sand Hill Angels, I tried to participate in, and create, small communities of women investors so that we could band together to not only reduce the workload, but through greater numbers, have greater influence.

This didn’t work out as well as I’d hoped and after a few failed attempts at various models, I gave up trying to bring women investors together.

Then in March of 2020, the world came to a screeching halt and I knew that the founders with startups working on things that I wanted to see in the world were in for a world of hurt. I wrote about this in a blog post called Are Early Stage Investors Investing?

What I most feared for these founders came true. Investors became less risk tolerant and the money tightened up.

That year, my focus was on my family. With no in-person events, my exposure to new deals decreased significantly. I was still getting pitches in my inbox and later in the year, accelerators and event organizers figured out how to do virtual events which, while not ideal, I think many of us were grateful for the opportunity to efficiently see more startups.

Similar to other investors with companies in their portfolio, my goal was to help my existing portcos survive. Because most of them had women founding teams, they had to get very creative very quickly. And they did.

Which led me to April 2023, and why I quit angel investing.

While there was plenty of dry powder out there with VCs raising funds the size of which make my chin drop, we saw a serious slowdown in investing in 2022. Investors were spooked by interest rate hikes, looming recession, the war in Ukraine, and general political unrest here in the US.

And then we had the SVB debacle. If there was any risk tolerance left at the end of 2022, it completely disappeared in March 2023.

With the collapse of SVB, we didn’t just lose a bank; we lost a critical piece of the startup ecosystem.

I agree with many who have opined on this and that we won’t soon recover from the loss in the startup world. Pitchbook released data that “VCs invested $46.3B in North American startups in Q1/2023 [which] is 46% lower than the same period a year ago.”

So the founders that did crazy, innovative things to make it through the Covid shutdown, who were nearly out of money and ideas at the end of 2022, now had what I saw as an almost insurmountable hurdle to accessing capital.

My checkbook, with an average check size of $15,000-$25,000, couldn't make a difference . As a solo angel investor unaffiliated with any groups or instituitions, my platform wasn't big enough to influence and change the startup ecosystem.

I was the change I wanted to see, and I know I made a difference, but it was time for others to pick up the torch.

While I absolutely love learning about new innovation and I loved helping startup founders (in moderation), I was out of gas. Just as Jacinda Ardern, former Prime Minister of New Zealand, said when she resigned, there’s not enough left in the tank.

In 2022, I made a few bad investment decisions. My husband reminds me that I learned a lot from them but I still feel like an idiot. I was hasty and didn’t do appropriate due diligence which I’ve frequently advised others on and even wrote about in Angel Investing: Due Diligence (Digging in with Investors).

I relied on my heart and not the data.

It takes a lot of time to stay current to make good investment decisions and I was no longer interested or motivated to put in the necessary time.

Regardless, I feel good about what I learned, what I invested in, and my contributions to the startup ecosystem as a vocal woman investor interested in expanding the power and influence of women, and improving people’s lives.

Over the last seven and a half years, I :

— Invested nearly $300,000 in 21 different companies ranging from pre-seed to seed, to Series A, and even Series B.

— Had one exit where I got my money back, one exit that is continuing to pay out due to the nature of the buyout, and one that I wrote off in March 2023.

— 19 of my investments are still in play with one doing incredibly well. Unfortunately I expect a few to fail this year for reasons I spoke about earlier in this post. Some would say that either I got very lucky or I didn’t take enough risk to have had so few failures at this point.

— Launched a podcast, started blogging, wrote and self-published the book Piloting Your Life, and launched a YouTube channel.

—Went to Slush in Helsinki twice to meet founders and investors in the Nordics to expand my world view.

—Participated in and/or moderated panels on world stages in places like Helsinki, Barcelona, and Berlin, and quite a few closer to home.

— Went on a solo investor trip to Paris, Estonia, Nice, and Berlin in 2018 to reduce my myopia as a Silicon Valley investor and native Californian.

—Was an advisor to startups for PanaceaStars in the UK.

— Considered and subsequently rejected the idea of starting my own VC fund, Class Bravo Ventures.

— Spent a year as an entrepreneur in residence (EIR) for Tech Futures Group.

— Was a Board Observer for one of my portfolio companies (SendaRide) based in Okalahoma City for four years.

— Went to Necker Island twice and played tennis with Richard Branson while there (in addition to other activities and interactions).

— Reviewed countless pitch decks, gave feedback and made recommendations to founders, and made innumerable introductions for underserved founders.

I will be forever grateful for the opportunity to be an angel investor in Silicon Valley. I found my voice. I found a broader purpose. I met amazing people around the world (and pissed off more than my fair share). I invested in some great startups that I expect will make me some money at some point.

I know I made a difference.

I took a short break and am now back with a stricter focus on women's health, especially for women over the age of 40. I am more disciplined and have greater focus on where my checks, network, and knowledge can truly add value.

When I was 8 years old, my dad, who was a fixed wing pilot, arranged for me and my identical twin sister Sherry to ride in a helicopter at an air show at our local airport in Hayward, CA. It was a short ride, but I remember saying to myself, one day I am going to fly a helicopter.

When we moved down the Peninsula from San Francisco to Redwood City, my husband and I would drive by the San Carlos airport, home to morethan a than a few helicopters, and every time we drove by, I told him that one day I was going to fly a helicopter. He got so sick and tired of me saying this that for my 38th birthday he gave me a discovery flight hoping I would shut up about it. It backfired because 10 months later I had my private rating and when I was 45, I got my commercial rating.

Becoming a helicopter pilot was one of the hardest things I'd ever done. As a girl I was not socialized to be interested in things that were necessary to learn and understand as a pilot. I had to learn the mechanics of the engine, physics of flight, and aerodynamics. At the same time, the easiest parts for me were communication on the radio, following checklists, and being able to do multiple things at the same time, all of which are necessary to be a good and safe pilot.

I essentially went back to school while raising two young children and leading a successful life sciences IT consulting firm. The weather didn't always cooperate, which meant training flights were frequently rescheduled. I started with one flight instructor only to fire him two months later and start all over with another flight instructor who effectively took me through my private check ride in March 2009.

The same year I earned my commercial helicopter rating, I was also experiencing perimenopause and started looking for something different after a decade of successfully leading my consulting business. One of my helicopter buddies suggested I become an angel investor. Although I'd been investing based on my dad's guidance for two decades, I didn't know I could invest in startups. The timing was right, and I jumped into it with Sand Hill Angels.

As with finally deciding to begin my training to become a helicopter pilot, I didn't overthink it and took the leap. It was a great decision.

As a Silicon Valley-based, midlife woman, angel investor, I quickly realized that it was assumed that I was part of the staff or someone's wife when I attended events. It was also assumed that I would help build the ecosystem to support women founders and create more women investors, while my men counterparts were free to focus on due diligence and writing checks.

I also witnessed that most of the podcasts, webinars, and books showcased or highlighted men and primarily white men. Women didn't have a seat at the table. There was very little diversity. It was all the same guys talking to each other or sharing the same information.

I started my podcast, Piloting Your Life, in September 2017, initially for those people who need to 'see it to be it'. In the second season, I shifted to focus on women founders, women investors, and those who supported the ecosystem to encourage more women to get involved. Money is power, and I wanted more women influencing what got funded—and therefore what exists in our world. 95% of the world was designed by and for men, and we make up over 50% of the population.

At the same time that I started my podcast, I started blogging once or twice a week to promote the podcast and share my personal thoughts on what was going on in my world. That's when I discovered I loved to write. In 2016 when I was first at Necker Island, I attended a workshop on how to write a book. In 2017 while talking to a friend about doing more speaking engagements, she said I had to have a book to be taken seriously, so I decided to write a book.

In November 2018, I heard a writing coach / editor / author on a podcast and decided that she was the one to guide me through the process. The next month, I decided on the topic, the title, and started the research. Nine months later, I self-published my book baby, Piloting Your Life, to inspire women over the age of 40 to design and live a life of our own creation. While the book was supposed to be a glorified business card, my beta readers let me know that it was so much more than that, and I quickly had to learn how to market a book.

Fast forward 8 years and a pandemic later, I'm now 56 and continuing the experiment called life. My husband and I launched Zeke and Terri Adventures to inspire people over the age of 50 to get out, get dirty, and go adventure (however you define it!) and better navigate modern midlife. I’ve been teaching Navigating Midlife for Women through Stanford Continuing Studies for the past three years and coach women, one-on-one, in how to really thrive in midlife.

I remain passionate about inspiring women over the age of 40 and 50 to live vibrant lives of their own creation. I love sharing what I've learned in the hope that one conversation, one class, one story, or one idea will give another woman permission to design and live a life of her own creation.