hurt family investments

Seven critical lessons learned in angel investing

I had dinner with my good friend and Bazaarvoice co-founder, Brant Barton, on Tuesday at the new Sway in West Lake Hills (yummy) and we talked about lessons learned in angel investing. It was on my mind as I’m doing an AMA (Ask Me Anything) webinar with my good friend and often investing colleague, Josh Baer, on Tuesday, Feb. 5 from 4-5pm CT (you can sign up here). During my conversation with Brant, I distilled down to seven lessons learned (in the spirit of Lucky7, of course). Brant is reading Jason Calacanis’s book on angel investing and told me that many of these are in there (maybe all of these, I haven’t read the book), so you may want to turn to that to really dig in as I’m going to do my best to keep this post short. My hope in sharing these with you is that it ignites more angel investing in Austin - it is vital to our startup ecosystem here. We are doing better on that front in Austin than ever before, but I believe we are only scratching the surface here. And I hope these lessons have an impact beyond Austin angels and startups as well.

Was 42 the answer to my life, universe, and everything?

Was 42 the answer to my life, universe, and everything?

Today is my 43rd birthday. As I think about the last year, my good friend and CEO coach, Kirk Dando, comes to mind. On page 141 of his excellent book Predictive Leadership, Kirk writes:

Why big life transitions are so hard and why it is so worth it to keep at it

Why big life transitions are so hard and why it is so worth it to keep at it

Life is like a record album, composed of songs to form the whole. From age 24 to 40, I had been playing the song "entrepreneur". I set a goal when I was 25 to one day found a tech company and take it public - by the time I was 40. Fifteen years later, I achieved that goal (my ultimate BHAG - "Big Hairy Audacious Goal"). Society didn't know about this very personal BHAG (only a few friends, my parents, and my wife did), and they expected me to keep playing the same song over and over again. This was natural, expected even. But as I wrote about in my "time is money or is money time" post, I was determined to step back and think deeply about my next move post being the CEO of Bazaarvoice. I didn't want to just set the same goal all over again (i.e., "now I'll found a sixth company and take it public again"). I knew I wanted to help entrepreneurs - I had always enjoyed doing so while I was at Bazaarvoice or Coremetrics but I had done so very sparingly due to the time constraints that I had (managing high-growth ventures takes a lot of time). I had love in my heart for Austin and thought I should do my part, along with many others like Josh Baer of Capital Factory, to help our scene evolve. So I jumped into that part of the arena - but in a more "grandfatherly" role as opposed to being the actual "man in the arena" (a nod to Theodore Roosevelt's powerful speech in 1910). As far as becoming an entrepreneur again and going back to that song, I had to think very deeply about it.

What I love about angel investing

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).

Why B2C is so hard to get funded in Austin

Why B2C is so hard to get funded in Austin

My good friend and the founder of Capital Factory, Josh Baer, wrote a post last year saying that he will invest in your B2C startup. Well, so will we. We wrote the first check for ROIKOI, which went on to raise well over $1 million, and also made investments in Bigwig GamesBlue AvocadoDeep Eddy VodkaDropoff, and Threadover the past two years. We were also one of the first checks for Wisecrack, but that is based in Los Angeles, and invested in the Series A for talklocal, based in DC. And we are investors in several venture capital funds, including Lead Edge Capital, which holds early positions in Alibaba Group, BlaBlaCar, and other large-outcome B2C companies but these are not in Austin so I guess I'm diverging from my point of this post. In any case, that is a total of eight B2C company investments (if you include Wisecrack and talklocal) out of a total of 33 startups we are involved with, representing 24% of our portfolio (and 18% if you exclude Wisecrack and talklocal).Real Massive also has a kind of B2C dynamic, even though it is B2B, so maybe I should count them too as they are Austin-based. But our primary focus is SaaS, for which we have holdings in 19 startups (57% of our portfolio). Both Bazaarvoice and Coremetrics were/are SaaS businesses and we have the most experience to bring to that category. SaaS is also far less risky than B2C, and that brings me to the real point of this post.

What I learned from my top three Lucky7 posts in 2014

December 5th marked my second year of blogging personally (I had previously been a corporate blogger for 7 years at Bazaarvoice as our CEO). I began blogging primarily as a service to entrepreneurs - a form of giving back to the community that I believe is the greatest force for change. If you are wondering why my blog is named Lucky7, it is as a tribute to my amazing mother, who passed away two years ago. Myfirst Lucky7 post on December 5, 2012 was a revisit of my manifesto written to the Bootstrap Austin community on March 15, 2005, months prior to starting Bazaarvoice. Much has changed in the nine years since and it wasn't unusual at all for Austin startups to raise seed capital vs. bootstrapping in 2014.

What I learned from my top three Lucky7 posts in 2013 … and my biggest busts

December 5th marked my first year of blogging personally (I had previously been a corporate blogger for 7 years at Bazaarvoice). I began blogging primarily as a service to entrepreneurs - a form of giving back to the community that I believe is the greatest force for change. I named my blog Lucky7 as a tribute to my amazing mother, who passed away last year. My first Lucky7 post on December 5, 2012 was a revisit of my manifesto to Bootstrap Austin on March 15, 2005. Looking back, it was clear I deeply cared about the development of our entrepreneurial community in Austin. That caring - and passion - drove a year of many highs in 2013. I've been actively investing in startups since December of last year with my wife, Debra, and I formally chose this as a career a few months ago, forming Hurt Family Investments. We've made 14 startup investments so far, 9 of them Software-as-a-Service (SaaS) companies. I've also joined the Advisory Board of 6 additional companies, all of them SaaS. Out of the 20 startups we are involved in, 16 are headquartered in Austin.