Creating personal flywheels to grow entrepreneurial assets

Finding harmony between passions, side hustles, and day jobs to accelerate your career as an entrepreneur

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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Creating personal flywheels to grow entrepreneurial assets

In my post about entrepreneurs as 1-person Venture Studios, I outlined the seven drivers of an entrepreneurial career which maximize entrepreneurial output over the course of a 30+ year career. These seven drivers are essentially “entrepreneurial assets” which we accumulate and take with us throughout our careers, even if we change jobs, move on from our startups, or decide to take 6 months off.

  1. Idea generation: the ability to generate diverse ideas or non-obvious ideas that only come with depth of exposure to an industry or problem

  2. Ability to assess potential: the ability to objectively assess ideas based on their potential upside and risks

  3. Network: access to talent and expertise

  4. Skills: functional skills like sales, engineering, product management, marketing, operations, hiring, community-building, etc.

  5. 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)

  6. 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).

  7. Resilience: the ability to start new ideas, work hard on ideas, and kill ideas – without burning out

This raises the question: how do you maximize the growth of these entrepreneurial assets?

The answer lies in finding harmony between your day job, side hustles, and passions, so that (1) energy you exert on a daily basis (including your day job) converts into entrepreneurial assets, and (2) the growth in entrepreneurial assets accelerates and compounds as you continue to invest your energy.

To put it another way, entrepreneurs can create personal flywheels for themselves which accelerate the accumulation of these entrepreneurial assets, similarly to how Amazon’s famous flywheel has fueled its growth. As Jake Singer, the author of The Flywheel (a newsletter breaking down different businesses’ flywheels) explains:

“A flywheel explains the success formula for a company or system. As X increases, it leads to more of Y, which in turn increases Z. As Z increases it flows back to X and the cycle begins anew...Like compounding interest, investments in one area of the business flow through to every other area of the business. These set off a series of accumulating advantages that the company enjoys over time.”

Whether you are currently building a startup or working for someone else, thinking through your potential flywheel can be a constructive mental model for trajectory within a day job, the side hustles you work on, and changes you may want to make.

In this post, we’ll go through two examples:

  • Max Nussenbaum, a former founder of a Y Combinator and Khosla Ventures-backed real estate startup which wound down in 2018. He spent two years exploring, but started a job a few months ago that is quickly growing his network, skills, and domain expertise in ways that are relevant to his future ambitions.

  • Brian Bosche, the founder of Slope, a creative work collaboration software which was acquired by SmartSheet in 2019. Brian now works as a product owner for the marketing and creative solutions at Smartsheet, and has created a powerful flywheel for himself through his side hustles.

Max Nussenbaum, former co-founder of Castle and current Program Director of the On Deck Writer Fellowship

Max is an entrepreneur and the former co-founder of Castle, a tech-enabled rental property management startup backed by Y Combinator and Khosla Ventures, which wound down in 2018. Max loves reading (he’s read over 1000 books), writing (he was a creative writing major in college where he also co-wrote his own musical), and community-building.

Since Castle, Max had mostly been freelancing, with a longer-term contracting gig thrown into the mix. During this time, Max had to exert additional energy outside of his freelance work to to build up entrepreneurial assets – he’d go out of his way to find an early stage startup to mentor or trying to ideate on new startup ideas with friends. A few months ago, he stopped freelancing and joined On Deck as the director of the writing fellowship, and decided to start his own personal weekly newsletter at the same time. In just a few weeks, Max went from someone who needed to exert additional effort to grow his entrepreneurial assets incrementally, to someone with powerful flywheel whose passions, side hustle, and day job are aligning to grow his network, skills, and domain expertise at an accelerating rate. Here’s what Max’s personal flywheel now looks like:

  • Loop #1: Max has initial credibility and skill as a writer, enabling him to build and operate a growing community of writers, which enables him to provide feedback to many writers, thereby increasing his credibility and skill as a writer.

  • Loop #2: Max writes a newsletter that helps him build up an audience. Continuing to write weekly improves his credibility and skill as a writer, making him a better operator of a growing community of writers, many of whom subscribe to Max’s newsletter, giving him more inventive to continue writing.

With this flywheel, Max has accumulated more entrepreneurial assets in the past 3 months than he had in the previous 2 years. With each day that passes, the growth in these assets is accelerating.

These assets are durable. If Max were to leave On Deck in the future, he would take the network, skills, domain expertise that he is accumulating with him, and he’d be able to leverage these assets in any future entrepreneurial ventures.

Brian Bosche, co-founder of Slope (acq by Smartsheet), currently Sr. PM at Smartsheet

Brian Bosche is the co-founder of Slope, a creative work collaboration product that Smartsheet acquired in 2019. Brian’s passions include basketball, photography and videography, and social media. When Smartsheet acquired Slope, Brian helped integrate Slope into the Smartsheet product and became the product owner for marketing and creative solutions. His day job requires that he get feedback from marketers and creatives about their workflow and use those insights to inform the Smartsheet’s product direction so they can grow within the marketing and creative segment.

Non-sequitur disclaimer: despite the fact that Brian plays basketball 10x as much as I do, I regularly beat Brian, including our recent 3x3 match up 2 years ago in Detroit, where I won 2 games out of 3 and scored on him consistently despite wearing tennis shoes. S/o to Zubin Teherani who was instrumental in that win. 

Brian is good at his core job, and being a product manager at a growing company is helping him sharpen some of his product management skills – which are relevant for any entrepreneur. But Brian has cultivated some side hustles that create alignment and harmony between his passions, these side hustles, and his day job.

The flywheel that Brian has configured is sharpening his skills as a product manager and creator, while simultaneously accumulating a network/audience at an accelerating rate (his social media followings are attributable to this flywheel). With each day that passes, Brian becomes even better positioned to launch another startup in the marketing/creative space if he wants to.

  • Loop #1: As part of his day job, Brian informs product decisions for Smartsheet’s Marketing and Creative Product. His influence on the product helps him have conversations with marketing and creative leaders to get feedback, and these conversations help him make better product decisions.

  • Loop #2: Through meeting creative and marketing leaders in his day job, he’s able to talk to some of them on his weekly podcast, CreativeBTS. The network of creative and marketing leaders he meets through the Creative BTS podcast also give him insights that help with his day job.

  • Loop #3: The CreativeBTS podcast increases Brian’s credibility and exposure in the creative/marketer space, increasing his social media followings. His social media posts further increase his audience and credibility as a creative, enabling him to get even better guests on the CreativeBTS podcast.

As a result of this powerful flywheel, Brian is accumulating entrepreneurial assets at a compounding rate.

If and when Brian eventually leaves Smartsheet, he will take his newly sharpened skills, massive audience, and increased domain expertise with him.

Building a flywheel for yourself sounds like a no-brainer, but it’s far easier said than done. Having a well-designed closed-loop flywheel is kind of like finding product-market fit – it’s so elusive that some entrepreneurs go their entire careers without finding it.

When writing this post, I tried to diagram my own personal flywheel. I found that there are pieces of my day job, passions, and side hustles (e.g. this newsletter) which are feeding each other and converting into entrepreneurial assets, but there are also some breaks in the chain. My flywheel is incomplete, and I consider myself in a state of exploration, simultaneously working on my day job and side hustles to try to find that alignment into a closed-loop flywheel.

After all, the only thing worse than an incomplete flywheel is a complete, closed-loop flywheel which sucks the life out of you because it’s not net-energy producing or isn’t aligned with your long-term interests.

While creating flywheels like Max and Brian have may seem like the ideal destination, it’s equally important to take time to explore, wander, experiment, and figure out what your ideal flywheel might look like so that it produces energy for you and is aligned with your long-term entrepreneurial interests. Much like you’d do customer research before building a product, it’s helpful to experiment, wander, and self-reflect before designing a flywheel for yourself.