There is a lot written on how to build a startup, but not enough written on how to build a solopreneur business. My go-to book for years has been Venkatesh Rao’s Art of Gig series, but his writing can be a bit challenging for beginners (these books are still in my must read category if you are committed to an indie path for more than a year).
Luckily, Jessica Lackey’s new book and workbook, Leaving the Casino, offers an absurdly useful guide on how to think through building a business on your own. What made it great, something I’m excited to recommend, is that it goes beyond tactics and pushes people to think through prompts, frameworks, and a well-thought-out process to go much deeper, focusing on the foundation level of your business.
It’s also pretty funny as she pokes fun of what she calls the “Entrepreneurial Casino”:
The Entrepreneurial Casino is a multibillion-dollar industry built around the dream of entrepreneurship, focused on selling quick and easy solutions to grow your fame and fortune. The influencers selling you these solutions are experts at using every marketing tactic in the book to ensnare you—scarcity, urgency, social proof, even sex appeal. It’s the course-based version of diet pills: fast promises of big results with little effort. This makes the tech platforms the ultimate winners of this game—you pay big bucks to advertise while your attention and data are commoditized and sold to the highest bidder.
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And when their strategies didn’t work? I was told to try again. Just invest a little more. Take the next course, upgrade to the premium mastermind, “fix my mindset,” and the oasis of success would finally be within reach.
And she goes on:
Because I’ve had such a variety of experiences—engineering, consulting, big corporate businesses, the startup world, and building my own business (first as a life coach and then as a fractional COO)—I can see across all of the different floors of the Casino.
The boss babes and manifestation girlies on Instagram showing off their luxury lifestyles.
The Twitter/X and YouTube bros promising that you can have six-figure revenue months just by writing content for one hour a day.
The B2B marketers turning LinkedIn into a sea of homogenized and flattened expertise that always leads with a “hook.” (Feels like a hook, line, and sinker to me.)
But I can use my experience to curate what does work in business and turn a torrential sea of information and shoddy promises into frameworks and tools specifically designed for small, knowledge-based businesses (like the ones I’ve built myself). The skills I honed in corporate strategy—diagnosing systems, analyzing trade-offs, and building sustainable solutions—are the same tools that can be applied to help entrepreneurs create profitable and sustainable businesses without sacrificing their values or well-being.
I have felt many of the same things and it’s not a coincidence that we both spent time working in strategy consulting before exploring an indie path.
A lot of people like to dunk on consulting but the best part of the experience was being exposed to hundreds of different global businesses and seeing how businesses actually make money. On top of that, we both DID ultimately leave consulting because sometimes it does get caught up in buzzwords, fads, and doesn’t quite deliver.
It’s an excellent guide for new indie freelancers who want to build their own solopreneur business but want more substance than the traditional tactic-style advice found online.
I also asked Jessica to do a little Q&A for the newsletter. You can read it here.
More highlights
When I started building my own business, I thought I’d see entrepreneurs taking a different approach—something more intentional, more authentic, and more human than the corporate world I’d left behind. I believed I was stepping into a space where creativity and individuality thrived. Instead, I walked straight into the Entrepreneurial Casino. Of course, I didn’t know it at the time.
The Casino doesn’t teach you how to build a business—it teaches you how to play business. Complex funnels, big teams, and expensive marketing campaigns are framed as essentials, even when they have nothing to do with the stage or structure of your actual business.
The advice peddled by the Entrepreneurial Casino isn’t entirely false. In fact, its power lies in its partial truths. The snappy advice we encounter—“Charge your worth,” “Delegate everything,” “Create passive income”—addresses real challenges in running a business. The problem is it simplifies complex issues into catchy slogans, glossing over the deeper work required to make thoughtful, aligned decisions. The cost of following this advice blindly is high: burnout, resentment, and a business that doesn’t feel like yours.
Most “celebrity” entrepreneurs have decided what model is right for them by nature of just being a brand figure. If they cultivated the Intimate-Impact model, they wouldn’t be a celebrity entrepreneur, right? So don’t assume that’s the only model for you.
The secret to their success? Most of these influencers got in the game early and built up followers and influence when the market was less saturated, customers less discerning, and platforms much less “pay-to-play.” Their marketing approach works because they fuel it with so many expenses: webinar and funnel software, a content creation team, sales assistants and appointment setters, and paid ads.
In my own business, I’m not optimizing for increased revenue. I know what I need to bring in from my business to fund my life, which is my goal.