Helping Founders Sharpen the Saw
What We Learned from Our First Unusual Academy
This time of year — despite all the hustle and bustle and negative rhetoric in the news — I try to take time to reflect on the good in all the people around me. Even if my daily contemplation consists of listening to a couple songs on a short walk, I’ve noticed it makes a big difference in how I experience things. As I’ve mentioned before, I’m from Georgia — so it probably comes as no surprise that I’ve been listening to Eric Church’s new album. One particular track, ‘Some of It,’ resonates strongly with me — especially as we just wrapped up our first Unusual Academy.
Over the past three months, we were fortunate enough to roll up our sleeves and work closely with nine founding teams. Like the “1.0” of anything, there was some great, some good, and some “need to improve that for next time.” No different than any startup.
Unusual Academy has one purpose: to provide an unprecedented, experiential learning environment for early stage entrepreneurs to gain the knowledge, tools and network they need to overcome the seven highest-stakes obstacles startups face at the early stage. From end-to-end, the experience is designed to give these founders an unfair advantage. We think of it as an Iron Man suit, turbo-charging their raw skills, empowering them to tackle the most important challenges ahead, and ensuring that they can confidently walk into any investor meeting to raise rocket fuel financing for the next stage.
We thought long and hard about the best format for the Academy. At Unusual, we’re convinced that entrepreneurship is a craft best learned through doing. And like anything worthwhile in life, the rewards come after hard work and some sacrifice. Accordingly, the Academy asks founders to invest their time, and open themselves up in order to grow. In exchange, they’re exposed to world-class entrepreneurs and operators who share the specific challenges they themselves faced and tactics they applied — tactics that both failed and succeeded. Participants are then required to apply these ideas and learnings to their own startups in interactive, concrete, and actionable ways. It’s tough sledding in a compressed timeframe, but we’ve already heard from founders that it’s changed the way they make decisions and run their teams.
To give you just one of many examples, instructor Billy Bosworth, better known as the CEO of DataStax, came in to share exactly how demanding and overwhelming it was to step into the chief executive role in 2011. The company still had a lot of ground to cover on building the right product, the right team, and prioritizing literally hundreds of urgent needs and projects. He presented the actual prioritization matrix he used to make key decisions that have gotten the company to where it is today. Beyond that, he offered his direct feedback as every founding team created and presented their own matrix of prioritized challenges and an action plan to resolve them. Every participant left with a clear path of execution to share with their team.
We specifically chose the seven obstacles we covered and invested the better part of a year working with hand-picked, high-profile practitioners who have successfully navigated each — including author Adam Grant, Wealthfront CEO Andy Rachleff and sought-after executive coach Maggie Hensle. To choose these seven topics and instructors, we leveraged everything I know investors are looking for at Series A, and that my Partner Jyoti Bansal learned building AppDynamics, and now Harness from scratch. Then we went out and found the absolute perfect people to teach the content and run interactive exercises that would have lasting, real-world impact.
The Academy’s goal isn’t to be overly prescriptive about process. I’ve seen time and again how that doesn’t work because every entrepreneur’s journey is unique and requires very custom decision making. Instead, the program provides access to examples, tools, process recommendations, and people that ultimately improve founders’ ability to execute.
An entrepreneur’s judgment is her most valuable skill — judgment about markets, co-founders, employees, investors, product directions, sales, etc. The challenge for many first-time founders is that judgment comes from experience — from understanding how others have solved similar problems, and from experimenting, failing, and succeeding again and again. Given this first principle, we built the content and delivery for Unusual Academy to rapidly hone the judgment of every participant.
The way venture capital operates today, there’s an enormous supply of capital available for companies that can successfully navigate the seed phase and tell a good story about their market opportunity, product differentiation, and go-to-market strategy. But there’s another trend I’ve observed recently: founders’ hiring judgment, emphasis on culture, and leadership skills are carrying more weight with investors than ever before given how competitive the ecosystem has become.
Unusual Academy is built to focus intensely on these capabilities. And while we still have a lot to improve, we’re thrilled to hear that it was a valuable experience from every participant in our Alpha Cohort. As one of these founders expressed to us in an email last week:
“The Academy played a large part in me getting comfortable with this new product strategy, so I can’t thank you and your team enough for the opportunity to be a part of it.
I’ve taken my team through several of the sessions — Ken’s storytelling exercise, Andy’s presenting to win framework, Maggie’s mindful leadership exercises, and I’m now following Jyoti’s customer development playbook in listening/selling to more carriers and TPAs.
There are too few opportunities for us startup CEOs to ‘sharpen the saw’ because it’s easy to tell ourselves that we’re too busy cutting. This was one of the best ‘sharpen the saw’ experiences in my startup journey, and it’s already paying dividends for us. I’m forever grateful to you and your team for that.”
Based on this feedback, we believe ‘Some of It’ was a big hit. A sincere thank you to everyone who applied (all 500 teams!), and all who were involved in bringing this useful content to life. Onward!
