I've spent the last 25 years in and around the software industry, first as an investment banker, then as a corp dev guy, marketer, founder, CEO, and finally as an investor. I invest in SaaS and software-enabled businesses, and increasingly I focus on those designed to mitigate climate change, or help humans adapt to its effects.
Unlike most angel investors, I maintain a concentrated portfolio of only a handful of active investments at a time. This allows me to dig in deep to each business and be more constructive with my advice. In some situations I join the board.
Throughout my career I've had tremendous mentors, and I try to return that good fortune by being a true friend to the next generation of entrepreneurs (whether I'm an investor, or not). As an advisor, I'm best known as a go-to-market specialist, having excelled in marketing and sales, but I have hard-won experience along the entire entrepreneurial journey from concept to exit.
Personally, I am most fulfilled by the human aspects of business: leadership, big decisions, org design, hiring and management. I'm plenty comfortable with product and finance, but it's the living, breathing part of business I like best.
For most readers, that's all you want to know. But for those who really want to know me, my life story is pretty much detailed below. If you're thinking of collaborating with me, it might be worth understanding how I ended up here at the Climate Cloud.
I grew up just outside Buffalo, NY – Clarence, to be specific. If you also grew up in Buffalo, we'll have an immediate connection around five things, two of which are professional sports and the other three, food. None of the five are healthy.
It was on Buffalo's frigid Black Rock Canal that I learned to row during high school. That did two things for me:
- It taught me how to persevere amidst discomfort, which turned out to be very useful when I started my company; and,
- It led to a call from Princeton's freshman coach, Mike Teti, who heard I was good at making boats go backwards.
I ended up getting a degree in economics at Princeton and rowing all four years. Mike is a three-time Olympian from the wrong side of Philadelphia who employed a coarse approach that's no longer permissible (I loved it). In contrast, varsity coach Curtis Jordan allowed us to succeed or fail under our emerging agency, which was good preparation for adulthood and entrepreneurship.
My teammates were an exceptional group of people who -- like a cliché wedding toast – made me want to be a better person. Many of us remain very close.
Hambrecht & Quist
My first job after college was as a corporate finance analyst at Hambrecht & Quist, the original tech-focused investment bank (now absorbed into JPMorgan).
H&Q was known for its IPOs of Apple, Genentech, and Netscape, but also for hiring truly good people. Two in particular were Andy Kearns and Jim Sullivan, who invited me into their software practice when the healthcare bankers had had enough of my #NUM!s and REF!s.
Andy and Jim taught me finance, attention to detail and how to serve clients well. I later moved to the research team where Jim Pickrel taught me the software industry (it's a little different now), and importantly, how to write.
In 1999, Dot Com mania was in full effect and I couldn't resist jumping to a Kleiner Perkins-backed start-up, e.piphany, which was founded by the now legendary Steve Blank. I was put in charge of managing the IPO process internally, and had the great pleasure of working with Steve to translate his vision into a Plain English S-1 that would pass muster with the SEC.
After that IPO, we had a silly market cap of over $10B, and we used it to acquire seven companies. Eventually the bubble burst, we all fell back to earth, and the company was ultimately sold to SSA Technologies (now Infor) for...well...a lot less than $10B. That was unfortunate, because the core of that company was an incredible product built by exceptional engineers.
Who knew marketing software was going to be a thing?
e.piphany was a roller coaster, and taught me that what looks good on PowerPoint can be difficult to execute in real life. In the process, I received tremendous mentorship from Phil Fernandez, who went on to found Marketo, and Kevin Yeaman, who is now CEO of Dolby Laboratories. Again, I was lucky to spend time at an organization filled with great people.
The Dot Com boom and bust left me with strong opinions on how to build a business:
- Raise as little money as possible, if at all;
- Focus narrowly at first, then expand deliberately; and,
- Remain humble, or at least pragmaticaly paranoid.
There are thousands of examples of entrepreneurs succeeding with just the opposite approach. In fact, Silicon Valley seems to be doing just fine without me. I've missed out on a lot of upside due to my Dot Com emotional baggage.
But I can say that my approach works. After leaving e.piphany, I started Software Advice, a marketplace connecting buyers and sellers of B2B software. We curated user-generated reviews and ratings, and excelled at content marketing, search engine optimization, digital advertising and high-velocity inside sales.
Software Advice was bootstrapped – like really bootstrapped, not fake bootstrapped, like not even my mom had a dollar in that company. After roughly a decade of toil and growth, we sold to Gartner. That proved to be a fine home for the team. I hear the business has grown, and is approaching $100M in revenue. That feels good.
There were a lot of things that made Software Advice successful, but if I had to pick a few, I'd start with our execution. We didn't spend time raising money, networking, or speaking at conferences; not that these are bad things, but we just decided to stay heads down, every day, and make sure stuff got done.
Second, we hired great raw materials. We threw away conventional wisdom about college degrees and experience, while doubling down on candidates with grit, clock speed and a chip on their shoulder.
Finally, we built a lot of software to optimize internal operations until every knob and dial was turned to perfection. A lot of what we built ourselves back then is now available commercially from companies such as DialPad, Calendly, Outreach, et. al.
At Software Advice, I was extremely fortunate to have received incredible leadership from my business partner, Austin Merritt. He was only 24 years old and nine years my junior when he joined the business, but he schooled me on execution and discipline. He remains a close friend and collaborator.
Lever & Dial
While we never took outside capital at Software Advice, I was very lucky to get plenty of free advice from Greg Goldfarb at Summit Partners. When I left Gartner, Greg invited me to co-invest in TSheets, which kicked off my independent SaaS investments. I advised TSheets on digital marketing and in less than two years they had a very successful exit to Intuit. Greg then brought me into a few of his other companies.
To formalize this new invest / advise gig, I dragged along two former teammates from Software Advice, Houston Neal and Cody Lee, experts in SEO and SEM, respectively. Together we operated as Lever & Dial, and it was great while it lasted.
Advanced Leadership Initiative
In 2019, I was feeling restless, and I came across an opportunity to go back to school through Harvard's Advanced Leadership Initiative – a one-year program dedicated to pivoting successful leaders toward solving society's most pressing problems.
It seemed crazy to give up a comfortable life in Marin Country, California, and move my family of six to Cambridge. However, my wife, Lauren, reminded me that I am a little crazy, and I've always been rewarded when I take calculated risks.
At Harvard, I focused my my time and effort on getting a crash course in climate change. I learned a lot about climate science from Daniel Schrag, including the thing that scares me most: CO2 doesn't just fall out of the atmosphere like particulates, so we're essentially stuck with the damage we're doing – unless we somehow figure out how how to suck CO2 out of the air, which we won't...not soon enough.
I took a fascinating seminar with Merchants of Doubt author Naomi Oreskes. To consider how mankind can overcome something as daunting as climate change, we dug deeply into past achievements, such as mass manufacturing, the Moon Landing, and the creation of the Internet.
The takeaway: our government has been a surprisingly nimble first-mover behind many of our country's most impressive achievements, but is routinely discredited by its biggest beneficiaries (i.e. Industry).
Finally, I refreshed my economics background with a very engaging Energy Economics course taught by MIT's charismatic Chris Knittle.
The Climate Cloud
My experience at Harvard led me in many directions as my mind exploded with ideas (none of which turned out to be original). I dug into demand response, thermal energy storage, solar development, and even explored a forest carbon sequestration opportunity in Montana.
Ultimately, I gravitated back to the familiar territory of software. It turns out there is tremendous opportunity to play a role in addressing climate change while leveraging my experience in software and entrepreneurship.
This blog is my forum for sharing my past experience along with my new learnings and interactions with the entrepreneurs and investors who are making a difference in the Climate Cloud. My hope is that through this blog, I will engage with this community and find opportunities to invest in and advise the most impactful of these ventures.