Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes essays, interviews, and more about building entrepreneurial careers. This isn’t startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal. I’m a former startup founder, the co-author of a book on seed fundraising, and am on the Early Stage Startup team at AWS.
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If you look back at a successful entrepreneurs career, you usually find a point where they had their break – they (1) came up with a good idea, (2) committed to it, (3) built it into a successful company – even if there are pivots along the way.
If this is the answer to building a successful entrepreneurial career – just make your break by building a successful business – then why am I writing this newsletter?
If that were the answer, then we’d have to leave a lot to luck. It also implies that the only way to make progress on an entrepreneurial career is by taking the leap of faith to start a company and succeeding. But success isn’t something we can fully control.
Part of my motivation for writing this newsletter boils down to two beliefs I want to explore: (1) building a long entrepreneurial career is just as much about the things we do outside of company-building than it is company-building, and (2) since success is never guaranteed, we need a way of thinking about entrepreneurial career progress that’s based on inputs we can control.
So I asked, what if instead of zooming in on the inflection points of success in an entrepreneur’s career, what if we zoom out and looked at an entrepreneur’s career over a 30-year horizon?
Over 30 years, an entrepreneur will have dozens of ideas, will work on some, will kill others, will double down on growing some ideas into companies, will have some of the companies fail, and will achieve varying levels of success. Along the way they will also work on developing their skills, network, and financial resources which help them get better and better at building companies.
If you compress all of those parts of a 30-year entrepreneurial career into a single point in time, it would look a lot like a venture studio.
Venture studios are company builders – they source ideas, figure out which ideas should be resourced, and launch these startups by leveraging by leveraging their platform (shared design, engineering, business development, fundraising, and legal resources) and a common methodology for experimentation and company building.
Therefore, venture studios provide a productive framework for optimizing the output of an entrepreneurial career by focusing on the controllable inputs.
If we think about entrepreneurial careers much like a venture studio thinks about their portfolio, then the output of an entrepreneurial career is based on this output equation:
Output = (High quality ideas) x (speed of quality execution) x (# of shots on goal)
We can break these variables into 7 different drivers of an entrepreneurial career – the controllable inputs that entrepreneurs can work on.
Seven Drivers of an Entrepreneurial Career
High quality ideas: (idea generation) x (ability to assess potential)
Idea generation: the ability to generate diverse ideas or non-obvious ideas that only come with depth of exposure to an industry or problem
Ability to assess potential: the ability to objectively assess ideas based on their potential upside and risks
Speed of quality execution: (network) x (skills) x (domain expertise)
Network: access to talent and expertise
Skills: functional skills like sales, engineering, product management, marketing, operations, hiring, community-building, etc.
Domain expertise: expertise on an industry (e.g. entertainment, education, web design), a market (e.g. VCs, restaurants, financial institutions), or a technology (e.g. machine learning, blockchain, advanced manufacturing)
# of shots on goal: (financial resources) x (resilience)
Financial resources: the money you have to fund new ventures (including savings that would allow you to spend time working on something without a paycheck).
Resilience: the ability to start new ideas, work hard on ideas, and kill ideas – without burning out
For a venture studio to survive, they need to be “good enough” at all seven of these drivers, and they need at least one driver where they have some secret sauce that sets them apart. The same is true for entrepreneurs. Building an entrepreneurial career is all about optimizing this equation in a way that works best for you.
This framework helps us understand why it’s so valuable for entrepreneurs to get their first rep at starting a startup. If you’ve never started a company before, getting your first rep results in a step-function improvement across many of the seven drivers in a very short period of time. It’s the fastest way to significantly close the gap on becoming “good enough” across these drivers. For example, here’s a self-evaluation of my own progression, before and after my first startup (red is zero, yellow is making progress but not yet at the bar for “good enough”):
This framework raises a pretty big question: what are the ways entrepreneurs can maximize the output of their career? Put another way, how should an entrepreneur work on getting “good enough” across these categories while developing their secret sauce as 1-person venture studio?
That’s a complicated question which will require a lot of writing and exploration to answer. But in this post I’ll unpack two different methods – space-focused and superpower-focused – using two examples.
Space-focused vs. Superpower-focused approaches
Optimizing all seven drivers while being a generalist is impossible. If you’re a generalist and are elite in even a few of these seven drivers, then you would already be a billionaire. However, if you’re able to pick a space that you’re passionate about, then it’s possible to become elite for several of these factors within the constraints of that space. This is the space-focused approach.
Meet Matt Sandler, a 1-person music & entertainment venture studio
Matt majored in music performance at UCLA and started his career as a professional saxophonist before joining a small startup in 2009 and catching the startup bug. Using his background as a musician, he created the first iPad app for sheet music, which grew into Chromatik (“Spotify for musicians”), which he ran for 6 years, building relationships with some big names in the music industry (peep Bruno Mars’ single investment on Crunchbase). After Chromatik, he joined the AWS Startup team (where I met Matt) and simultaneously joined Techstars Music as an Entrepreneur-in-Residence. Aside from learning the operational chops one learns at Amazon, Matt spent his time working closely with the Alexa fund, learning about the future of voice, before changing roles to start working on new projects for Amazon Music.
Matt picked a space he was passionate about – music & entertainment – which became a through-line for everything he’s done in his career. Matt’s passion and background in music set him apart as an entrepreneur (there aren’t many former professional musicians in the startup world). From there, everything else was optimized as a by-product of that focus. When it comes to the music & entertainment space, Matt is elite at three of the seven drivers of entrepreneurial career: (1) Ability to assess potential, (2) Network, (3) Domain Expertise. You can see this illustrated in practice by the fact that Matt can come up with an idea and basically start a company with a tweet, despite only having 2,450 twitter followers and only getting 2 retweets. Matt’s network is optimized around media.
Cherie Hu @cheriehu42major labels are eating the blogosphere streaming services are poaching journalists to help run their music podcasts all the major trades are now owned by the same company and, of course, newsletters now is an ~ interesting ~ time for music media to say the least
I don’t think it’s possible for someone to be a generalist and be in the elite in three of those seven drivers. But by focusing on a space, it’s possible.
But what if you don’t have a space that you’re super passionate about? That’s where developing superpowers come in.
Meet Erik Torenberg, 1-person venture studio focused on community-building
Erik doesn’t have a space he’s focused on like Matt. Instead, Erik has focused on developing a superpower that can help him start ventures in many different spaces – community building.
Long before he was successful, he was honing his craft with community building in Detroit in 2013. Erik got his early reps in community-building through rap battles, and he started working on a startup called rapt.fm, which was an online platform and community for rap battles. After moving to San Francisco and deciding to move on from Rapt.fm, he joined Ryan Hoover on the Product Hunt founding team as the first employee. Erik spent all of his time focused on community-building with a fast-growing startup that had community as it’s foundation. Even while at Product Hunt, Erik did community-building on the side, hosting monthly dinners for people who were looking for their next thing in tech (whether that was starting a new company or changing gigs). By the time Erik left Product Hunt, he was already viewed as a community-building expert and had cultivated an unrivaled network for a 20-something-year-old as a by-product of his community-building. This network helped him co-found Village Global, a network-driven VC firm that relies on a community of Venture Partners making investments. Meanwhile, that monthly dinner series he started years ago grew into On Deck – a fast-growing startup that coins itself as a community ”where top tech talent goes to explore what's next.”
Community-building has been the through-line for Erik’s career as an entrepreneur. Erik is a generalist, expressing interests in education, cryptocurrencies, and various other spaces. Of the seven drivers of an entrepreneurial career, Erik has been singularly focused on community-building as a skill. As a by-product of that skill (and the act of practicing it), Erik has built as strong of a personal network as anyone I’ve seen. Erik focused on a single superpower, community-building, and became a 1-person venture studio based on that superpower and an elite network he now has thanks to his community-building. If I had to guess, I’d say that Erik will start something else in the next few years, and community-building will be at the center of it.
But what about the rest of us?
Matt and Erik found their ways to becoming compelling 1-person venture studios unusually early in their careers. For most entrepreneurs (myself included), it’s going to be a longer, windier path. I personally don’t think I’m ever going to have a space that I focus on, and I haven’t pinned down as well-defined of a superpower as “community-building.” But even without full clarity of what my 1-person venture studio’s secret sauce will be, this framework is helping me align the ways I spend my time today with my longer term goals. I can be intentional about continuing to develop as an entrepreneur, even though I’m not currently building a company.