Top 3 Investor War Stories

In our interview series we embarked on a journey to explore the experiences and insights of seasoned investors. Through it we uncovered the worst and best investing experiences encountered by these individuals and the valuable advice they have to offer. By interviewing these investors, we gained unique perspectives on the challenges and pitfalls that can arise in the investment landscape. Join us as we delve into their stories, learn from their mistakes, and gain valuable insights that can help navigate the complex world of investing.


Interview #1:

We interviewed Stephen Nicolle as a part of our Fund Investor Series. This is his story…

Stephen Nicolle is a founding partner of Island Capital Partners, an early stage venture capital fund based in Prince Edward Island, Canada. After many years of experience as CEO of international venture-backed technology companies in telecom, video surveillance, wireless convergence, and healthcare IT, Steve now focuses on advising young entrepreneurs and the companies they lead.

What is your war story? 

In the middle of the night before closing the acquisition of one of the companies I was CEO of, our legal team called me to say they had discovered that the company owned a condo in downtown Toronto – did I know anything about that? I did not. So we hooked a cab (pre-Uber days) and knocked on the door. Turns out one of the original founders was using it as slum housing for tech immigrants. Never a dull moment.

Any advice? 

When you think you’ve paid enough attention to the founding team … pay some more.

Interview #2:

We interviewed Marcia Dawood as a part of our Women Investor Series. This is her story…

After spending an award-winning career in sales, marketing and operations for one of the largest education providers, Marcia Dawood now works on making people’s dreams come true. Marcia is an investor in over 200 early stage private companies. In addition to her own investing, she is a Venture Partner in Mindshift Capital, an early stage fund focused on investing in post-seed early-stage companies in the U.S., Europe and Middle East. Marcia is also Chair of the Board of the Angel Capital Association, the largest angel professional development organization in the world and has led the ACA’s Marketing and Membership Committee and Growing Womens’ Capital group.

What is your war story?

I made 2 investments early on. One had a successful exit after 8 years but the other went out of business early on because the founder simply didn’t care enough about the company and when the company was tight on cash, he bailed. Not that unusual of a story but the company had won a BUNCH of awards, pitch competitions and had a ‘follow the crowd’ mentality from investors. It made me look a lot differently at companies ‘winning awards’. Sometimes the founder is just a good salesperson, not a good CEO…

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Any advice?

I started a podcast, the Angel Next Door, for the ACA specifically on helping anyone who is interested to become involved with early stage investing. The best advice I can give is to join a group or a fund and learn from your colleagues so you don’t do this alone. I’d also advise those raring to go to wait to make a first investment until after seeing several companies and getting a little bit of a feel for how experienced investors evaluate them.

Interview #3:

We interviewed Brad Johnson as a part of our Fund Investor Series. This is his story…

Brad Johnson believes the “world deserves craft.” As the General Partner of Third Craft Partners, Brad joins with and accelerates those passionate challenger food and beverage brands that believe the world deserves better. Brad brings deep experience in product management, brand management and high end luxury real estate development to his work at Third Craft.

What is your war story?

We spent 6 weeks doing heavy due diligence on a brand we loved and were about to bet the entire fund on it. At the last minute a West Coast VC learned about it and invested in the same day. We lost the deal. The company was worth $45m when we were considering investing and it got scooped up. They just raised a round at a $400M valuation just 18 months later.

Any advice?

Have patience.


What's your worst investing experience and what advice do you have to share? We'd love to hear from you, so send us your investing highs and lows!