Inside Thoughts


It’s Not Worth It

Three times in my career, I’ve had firsthand experiences with CEOs who behaved badly. I’m not talking about poor judgment as it relates to business decisions; but actions that were unethical, immoral and/or illegal. In each of these, the damage to the CEO and the company was significant. In addition to my firsthand experiences, I’m […]


Saw this meme emerging on Twitter the other day: #TriggerA(fill in a group)in2Words I’ve been pretty good about keeping a positive attitude for a while now about the current state of our country so I was surprised how much seeing this meme bothered me. I couldn’t shake it all weekend and finally figured it out […]

Four Questions

Over President’s weekend, I spent 4 days with friends and family deep in the backcountry at an AIARE I Avalanche safety course with our friends at Payette Powder Guides. Split between classroom time in the Yurt and field work while backcountry skiing in the Payette National Forest, it was incredibly enlightening and I recommend the […]

What Does Your Company Stand For?

Yvon Chouinard’s been my business hero for as long as I can remember. Let My People Go Surfing is one of my favorite books of all time (not favorite “business” books, but favorite books, period). The way Patagonia has gone about building a global brand while staying true to the values that Yvon founded the […]

The Future Of Tattoos

Years ago, I was interviewing Alex Iskold for the Managing Director position of our Techstars NYC program. We had a great visit and towards the end he asked me “What’s one particular investment you’d love to make?” I responded “Find me a company that’s going to solve the problem of dealing with America’s new love […]

Making The World A Better Place, One Startup At A Time

When you’re building a business, you tend to be so heads-down in the weeds that you forget to look up once in a while and see how much progress you’re making. That happens to us here at Techstars too, though I’ve noticed a trend lately though that has me incredibly excited about the work we’re […]

Trying Twitter Again

Twitter. I suspect most people engaged on the platform these days have either A) developed a love-hate relationship with it B) have carefully curated their streams or C) are somewhat masochistic. It’s been over half a year since I’ve engaged with twitter. I needed a break as my feed had devolved into a cesspool of […]

The Global Startup Community Marches On

Last week Ryan Broshar and I were in Ho Chi Minh City, Vietnam visiting the Inspectorio team (graduate of our Techstars Retail Accelerator in partnership with Target where Ryan is the Managing Director). It was my first time back there since 2010 and I was gobsmacked at the changes that have occurred; gleaming new skyscrapers fill […]

The World Needs More Ryan Connollys

There are people born to be entrepreneurs in this world and Ryan Connolly is one of them. I got to know Ryan as an associate at Techstars and while he’s not trying to build the next great venture-backed tech giant, he’s every bit as entrepreneurial as those who set out on that path. Three and […]

Pilotworks: The Next Great Food Company

  While my blogging slowed over the last little while, the pace of investments I was part of at Techstars certainly didn’t. One of the companies I’m most excited about is Pilotworks (Techstars NYC 2015) which we co-led their $13M Series A last fall and I now serve on their board of directors. Founders Nick […]

I’m Back

I used to blog a lot. I was passionate about it and really enjoyed the experience. However, over the last year or two, my writing slowed to a trickle. Perhaps I realized that I was one of a few hundred white male VCs blogging about tech and startups and there really isn’t that much unique […]

The Tao of Brad

Last week I was on a long mountain bike ride and wound up spending a few hours grinding away on a particular difficult situation one of the CEOs I work with was going through, when some advice Brad Feld gave me years ago popped into my head and I knew it was just what my […]

Financing Round Nomenclature Revisited

When I started investing in startups a long time ago, the labeling of financing rounds was as simple as the Sesame Street alphabet song – A is for Abbey, B is for Bert, C is for Cookie Monster; ok, you get it. The rounds were named for the purpose of identifying shareholder rights in a particular […]

Helping An Entrepreneur See His Work Come To Life

This summer, I had the privilege of spending time with my friend Chris Burkard in the remote Westfjords of Iceland which I wrote about here. Yesterday, Chris announced a Kickstarter campaign for his film “Under An Arctic Sky.” Here’s the trailer: If you’re an outdoor adventure junkie like me, you’re surely familiar with Chris and […]

A Beautiful Continuum

The first time I met Natty Zola was in the old Techstars bunker back in the summer of 2009. He and his co-founder Nate Abbott had recently started a company called Everlater and were going through the Boulder Techstars program. They told me their story about chucking their Wall Street jobs, traveling around the world together […]

Before Voting, Think About Your Daughter

My daughter turned 18 last month and I’m so grateful that she grew up in a country that has been steadily moving towards true equality for women. America’s slow march towards equal rights for all has fostered an environment where young women today, more than any time in history, finally believe they can accomplish anything a […]

Hacking Reference Checking 

  We all acknowledge the critical nature of thorough reference checking as it relates to hiring or investing in someone. However, given that most people are reticent to offer a negative reference, most of us struggle with extracting the type of valuable feedback we’re seeking in order to make better decisions. Many years ago, a […]

The Music Never Stopped

“Music is a moral law. It gives soul to the universe, wings to the mind, flight to the imagination, and charm and gaiety to life and to everything.” – Plato Back in 2011, I walked into Topspin Media’s office for the first time and this bearded dude in a faded brown tee shirt popped out […]

The Toughest Person I Know

Two years ago, our dear friend (and my incredible assistant) Denise shared that she had been diagnosed with stage 4 colon cancer. It had metastasized to other organs and she would have to undergo very aggressive treatments immediately. We were all stunned. Everyone except Denise that is. She took it in stride and simply wouldn’t […]

This Is What The Apocalypse Looks Like?

Back in Q1, you couldn’t swing a dead cat without hitting someone advising startups that the world, as they knew it, was coming to an end. Venture dollars flowing to startups had decreased from $16B in Q3 ’15 to $12B in Q4 and VCs were telling anyone who would listen that nuclear winter was in […]

Start typing and press Enter to search