What I love about angel investing

Today is my 43rd birthday (you can read about what I learned over the past year inmy Lucky7 post about age 42). Looking back on my last year, I've grown to really love angel investing. My wife, Debra, and I run a family office that we call Hurt Family Investments. She takes the lead on philanthropic projects, and I take the lead on startup investing. For the past two years, we've invested the same financial amount in non-profits as we have in startups. We always agree on what to invest in - she has to meet the entrepreneurs before we make a decision - and that leverages the best of both of us. Debra is a contrarian thinker and was also born to entrepreneur parents. We both learned a lot about entrepreneurship growing up, and we actually started Coremetrics, my fourth business, together. She has terrific entrepreneurial instincts and there are a number of companies that I haven't started because I listened to her (thankfully), when I was playing the song "entrepreneur" on my record of life. Now, we are involved in 34 startups (mostly in Austin) and multiple VC funds that give us exposure to at least as many additional startups (you can see our portfolio here).

I've been playing a new song now (changing your song on your record of life is verydifficult as I describe in this Lucky7 post on big life transitions). My new song is harder to categorize as simply as "entrepreneur"; maybe "startup catalyst" is an appropriate name. "Startup catalyst" is more of a mosaic of activities that leads up to a cumulatively big impact. I want to look back 10 years from now, when I turn 53, and know that I made a big difference to our entrepreneurial scene here in Austin. That is what drives me now and I believe it is just as worthy of a mission in life as my original goal to found a company and take it public (I set this goal when I was 25-years old, shortly after taking the plunge into entrepreneurship). Both goals were and are about impact - creating jobs, new companies (former Bazaarvoice team members have started 22 companies and counting since leaving Bazaarvoice), and karmic ripple effects (philanthropic and helping to change the world for the better both through Bazaarvoice and these new startups).

I wake up every day energized to help the 34 companies in our portfolio. Every day that I'm in Austin I meet with two to three of the entrepreneurs that we've already backed to do anything I can to help them. And I'm constantly evaluating new companies - I've seen over a thousand pitches in the last two years. This is very intellectual work - you are always context switching and learning about new industries. One hour I've got my Edgecase hat on, the next I'm wearing my OneSpothat. Although our primary focus is SaaS (Software as a Service) investing, the business model that I've lived since 1999, the industries are varied and the challenges are unique. Every day is a mosaic of activities for me, and that is extraordinarily rewarding. I'm working my brain like never before. I read blogs, books, and all types of social media and I find that more and more of what I read relates to at least one of the companies in our portfolio. You get to put patterns together at a much broader scale than you do when you are focused on running a single company at a time, as I was with Bazaarvoice and Coremetrics before this.

 

Bazaarvoice was amazing - a truly incredible journey. But this new song is equally amazing - it is just a very different life and rewarding in a very different way. I've learned to be just as excited for the entrepreneurs we're helping as I was for my team at Bazaarvoice when we hit new milestones and infection points. We host events at our home for the portfolio company CEOs and last week had one of the first employees at Amazon keynote, telling us about how their culture evolved and diving deep into their hiring practices. These discussions are valuable and energizing. We are creating a community of CEOs that are helping each other, formed around our portfolio. I'm constantly tapped by VCs looking to invest in Austin to get a lay of the land of our scene here. This inevitability leads to me introducing them to several of our portfolio companies (I do this for our local VCs as well, of course). I'm able to negotiate discount rates from large vendors, like Amazon Web Services, as well as small ones, like a presentation training company, for our portfolio companies.

  Another huge benefit of angel investing is the impact it is having on our children. When we host those founder learning events at our home - or sometimes when we have entrepreneurs pitch us at our home - we have our daughter and son attend. To say this is inspirational is an understatement. Our children are getting terrific exposure to very passionate people who are determined to change the world in their own way. As they both have stated they want to be entrepreneurs themselves, the training they are getting is invaluable. I'll be happy for them whether they actually become entrepreneurs or not (they need to decide what song they want to play on their record of life), but no matter what I'm convinced that exposing them to this level of business learning will be helpful to their careers one day. I could write a lot about our financial strategy as angel investors in this post, but I'll save that for another time (for now, if you are curious, we roughly follow this strategy - but we intuited our strategy from watching others that got into angel investing before us, not by reading Jerry Neumann... although I think he is brilliant and a very talented blogger). My advice is that if you get into angel investing, you'll do better at it if you learn to love helping entrepreneurs as much as you loved being an entrepreneur yourself. It is very hard to get used to the new song on your record of life - your mind will want to pull you back to the old music - but if you stick with it, the music will get better and better. And maybe, just maybe, you'll cumulatively have a bigger impact than you did as an entrepreneur yourself (or however you made your money to get into angel investing)... I would love to hear from other angel investors and entrepreneurs in the comments below. Angels, what did I miss that you have learned and loved about investing in startups? Entrepreneurs, what have you seen from your most helpful angel investors?

 

Another huge benefit of angel investing is the impact it is having on our children. When we host those founder learning events at our home - or sometimes when we have entrepreneurs pitch us at our home - we have our daughter and son attend. To say this is inspirational is an understatement. Our children are getting terrific exposure to very passionate people who are determined to change the world in their own way. As they both have stated they want to be entrepreneurs themselves, the training they are getting is invaluable. I'll be happy for them whether they actually become entrepreneurs or not (they need to decide what song they want to play on their record of life), but no matter what I'm convinced that exposing them to this level of business learning will be helpful to their careers one day.

I could write a lot about our financial strategy as angel investors in this post, but I'll save that for another time (for now, if you are curious, we roughly follow this strategy - but we intuited our strategy from watching others that got into angel investing before us, not by reading Jerry Neumann... although I think he is brilliant and a very talented blogger).

My advice is that if you get into angel investing, you'll do better at it if you learn to love helping entrepreneurs as much as you loved being an entrepreneur yourself. It is very hard to get used to the new song on your record of life - your mind will want to pull you back to the old music - but if you stick with it, the music will get better and better. And maybe, just maybe, you'll cumulatively have a bigger impact than you did as an entrepreneur yourself (or however you made your money to get into angel investing)...

I would love to hear from other angel investors and entrepreneurs in the comments below. Angels, what did I miss that you have learned and loved about investing in startups? Entrepreneurs, what have you seen from your most helpful angel investors?