brianshin
brianshin
Oct 28 · 5 min read

Getting Back In The Saddle

Startups are tough! Recent data indicates that over 90% of startups do not end up succeeding. There are grumblings that we’re at the tail end of a historic bull market. The days of startup growth at all cost may be over. So it is with this sunny context that I’m announcing that I’m leaving the comfortable investment world and starting a new company, searchable.ai, with 3 amazing co-founders: Nick Martin, Aaron Sisto, and Hung Nguyen. Great timing, I know! To compound matters, I’m also moving with my wife and kids from Boston to San Francisco, even as Boston’s startup scene is rocking and CA wildfires are raging. Why, you may ask??

Retired from Entrepreneurship

When my most recent two startup companies were acquired in early 2017, I thought that my time as an entrepreneur was over. After 8 startups and 7 exits, I was too burned out, too old, too slow. I decided to move onto a new role as a full time investor in technology companies. That way, I could still have the opportunity to work with great entrepreneurs while being able to be a step removed from the day to day rollercoaster of startup life.

By this point, I had been an active angel investor for more than 10 years in over 50 companies started by friends, colleagues, and people trusted by friends. Some of these companies include HubSpot, Misfit, Drift, Frequency Therapeutics, and Kayak. But I recognized that being a full time investor would require a higher level of discipline and diligence. I was very fortunate to have had some amazing learning experiences and to have led some really great deals as a technology investor with two fantastic firms, In-Q-Tel and Providence Equity Partners. But as I kept meeting with phenomenal entrepreneurs, a longing for the feeling of “creating something from nothing” kept bubbling up.

Honestly, even with this longing, I did not imagine that I would start another company. I had made so many mistakes as an entrepreneur and felt like at various times that I had let people down. The thought of starting from scratch again after so long just seemed incredibly daunting, especially with the stress that many startup founders endure.

Early stage companies can struggle for any number of reasons including market timing, strong competition, suboptimal execution, disagreements among founders, a lack of focus, and more. An often overlooked aspect hindering startup success can be the mental and physical toll that startups can take on founders and employees. As a startup founder, one can experience dramatic highs and traumatizing lows in the course of a single day. The role of CEO is often described as the “loneliest job,” because there are so many topics that can be difficult to discuss with colleagues or board members. CEO’s and founders often try to be strong for their teammates, but in the process may end up absorbing a lot of angst that can eat away at them.

Recognizing a Problem

But I started to see an opportunity that I couldn’t stop thinking about. It is a problem that people in the workplace run into over and over again. After significant research, I could not find a suitable solution. I asked some colleagues and they all said that they had the same sort of issues when they were working. So Nick, Aaron, Hung, and I started hacking on a new project to try to address these problems. I even set aside some money to self-fund this project thinking that I would not want to raise outside capital given all the additional expectations and pressures that would come with it.

We started to make some progress. We found that many companies experience the problems that we were seeing. The opportunity seemed real. So we dug into building a new technology to address this problem. That is when a good friend, Neil Sequeira, a leading venture capitalist who had backed my last company, suggested that we raise some venture capital to pursue this idea. In fact, he offered for his firm Defy Partners to lead our round.

Hemming and Hawing

I had a lot of hesitation. First, I felt that I had lost my entrepreneurial mojo. Entrepreneurs need to have optimism to be able to see a future that can be better than it is today combined with the drive to make it happen. I felt optimistic about us being able to improve how people work with this new technology we were building. But maybe I just lacked the self-confidence to go for it.

I highlight some of the challenges that I was going through because I know that there are people out there struggling with similar thoughts. Do you have an idea but you worry that you don’t have what it takes to be a founder? Maybe you just don’t know where to begin. Do you have a comfortable job and worry about the risks of starting a company? These types of concerns are partially why there are a lot of entrepreneurs under the age of 30. Why? Because younger folks tend to have lower opportunity costs. If you are struggling with the stress, loneliness, or financial pressures of “going for it”, believe me, you are not alone!

Deciding to Go for It

Defy Partners’ vote of confidence helped me tremendously. Having great partners (and a big challenge to dig into) really solidified the decision to go all in. Our founding team consists of Nick Martin, co-founder and Chief Technology Officer, Aaron Sisto, co-founder and Chief Scientist, and Hung Nguyen, co-founder and Chief Marketing Officer. Nick, Aaron and I had worked together at In-Q-Tel, a strategic investment firm working on behalf of the US Intelligence Community, where we made investments in innovative technologies that had the potential to help improve national security. Hung and I had worked together for years at our previous company, Visible Measures. Hung more recently co-founded and sold an analytics startup called Ozmotik, where I served as an advisor.

There are a bunch of things that I love about our founding team: 1) We have all started companies, so we know how hard it is 2) We have all worked together before at various times 3) We all have experience working with and building AI-driven systems and 4) All of us had to give up other opportunities to pursue searchable.ai full time.

Soon, we will go into detail in terms of what problem we are solving and what solution we are building. But for now, I just wanted to give a little background on our origin story while also sharing some words of encouragement for those of you out there contemplating developing the next big thing! Startups are hard; you never know how they are going to go. But despite some good reasons to the contrary, I decided that it was time to get back in the saddle and go for it. Very excited to be building something with great partners like Nick, Aaron, Hung, Neil @ Defy, and all the incredible folks who are backing us!

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Brian Shin

Co-founder & CEO, searchable.ai

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brianshin

Written by

brianshin

Co-founder & CEO @searchableai. Admirer and backer of entrepreneurs @vitalstage ventures