> ## Content Index > Fetch the complete content index at: https://www.ridiculouslyefficient.com/llms.txt > Use this file to discover other available public pages before exploring further. # Our Top Salesperson Built a Side Hustle. Our CEO Helped. - URL: https://www.ridiculouslyefficient.com/encourage-employee-side-hustles-ai-fluency/ - Published: 2026-08-31T16:00:00.000Z - Updated: 2026-08-31T15:59:59.000Z - Description: Our top salesperson made $6,000 in two days building websites with Claude, alongside his day job. Our co-founder and CEO encouraged it. The old script calls that a flight risk; the new math calls it the cheapest AI-fluency program a business can run. - Author: Marissa Brassfield - Tags: Vision-Execution --- title: "Our Top Salesperson Built a Side Hustle. Our CEO Helped." slug: "encourage-employee-side-hustles-ai-fluency" description: "Employee side hustles used to read as flight risk. Our top salesperson made $6,000 in two days with our CEO's encouragement. Here's the AI-era math." pillar: "Vision-Execution" secondary\_pillar: null publish\_date: "2026-08-31" status: "draft" author: "Marissa Brassfield" word\_count: 1830 keyword\_brief: primary\_keyword: "employee side hustles" secondary\_keywords: - "encourage employee side hustles" - "AI fluency" - "AI upskilling employees" search\_intent: "Informational" topic\_ownership\_cluster: "AI-forward leadership / future of work" people\_also\_ask: - "Should employers encourage side hustles?" - "Do side hustles make employees better at their jobs?" - "How do companies build AI fluency in their teams?" sources: - title: "Microsoft and LinkedIn 2024 Work Trend Index" url: "https://news.microsoft.com/source/2024/05/08/microsoft-and-linkedin-release-the-2024-work-trend-index-on-the-state-of-ai-at-work/" - title: "Sessions et al., Do the Hustle! (Academy of Management Journal)" url: "https://business.unl.edu/do-hustle-empowerment-side-hustles-and-its-effects-full-time-work-performance" - title: "Bankrate 2025 Side Hustle Survey" url: "https://www.bankrate.com/loans/small-business/side-hustles-survey/" - title: "PwC 2025 Global AI Jobs Barometer" url: "https://www.pwc.com/gx/en/news-room/press-releases/2025/ai-linked-to-a-fourfold-increase-in-productivity-growth.html" - title: "Microsoft 2025 Work Trend Index: The Year the Frontier Firm Is Born" url: "https://www.microsoft.com/en-us/worklab/work-trend-index/2025-the-year-the-frontier-firm-is-born" - title: "LinkedIn 2025 Workplace Learning Report" url: "https://www.linkedin.com/business/talent/blog/learning-and-development/2025-workplace-learning-report" - title: "FranklinCovey, Habit 7: Sharpen the Saw" url: "https://www.franklincovey.com/habit-7/" - title: "CNBC: Meet the companies encouraging side hustles" url: "https://www.cnbc.com/2021/12/22/these-companies-actually-encourage-staff-to-have-side-hustles.html" - title: "CNBC: Google's 20% rule" url: "https://www.cnbc.com/2021/12/16/google-20-percent-rule-shows-exactly-how-much-time-you-should-spend-learning-new-skills.html" internal\_links: - "https://www.ridiculouslyefficient.com/every-past-version-of-you-is-source-material-now/" - "https://www.ridiculouslyefficient.com/your-first-year-going-fractional/" - "https://www.ridiculouslyefficient.com/vision-execution-gap-sustainable-leadership/" created\_at: "2026-08-07T00:00:00-07:00" --- Every month, our all-hands opens the same way. We go around the room, 27 of us across time zones, and each person shares one genuinely good thing from their month, personal or professional. The ritual sounds small until you hear what people bring to it. At a recent one, our top salesperson's good thing came with numbers attached. He'd made $6,000 in two days building websites for local businesses with Claude. He has never written code for a living. He scraped his own list of businesses with no website, built each of them something polished in under an hour, sent 86 cold emails, and closed roughly 20% at $500 a site. All of it alongside the sales role he's still the best on our team at. My turn came a few shares later. I'd spent several weeks building an autonomous content system on top of 20 years of writing and ghostwriting, and I'd watched it start producing work that used to consume my whole calendar. Two decades in rooms like this taught me the old script for that moment. A leader hears a star performer describe a thriving side business and starts counting the days until the resignation email. Our meeting ran the opposite direction, and why it did is the most useful thing I can tell you about leading in the AI era. **TL;DR:** Encouraging employee side hustles is one of the fastest ways to build AI fluency inside a business. The skills someone gains building their own project stay in the organization and compound through everything else they do. Leaders who authorize this out loud trade the illusion of control for capability and for people who stay by choice. **About the author:** I've coached 500+ entrepreneurs and executives from 31 countries over 20+ years, including 8.5 years running the operations engine behind a leading entrepreneur community before co-founding businesses of my own. Since March 2023 I've run my practice on a 3.5-day workweek, and I build my own AI systems; the autonomous content engine I mentioned above runs on two decades of my published writing. My work lives in [the vision-execution gap](https://www.ridiculouslyefficient.com/vision-execution-gap-sustainable-leadership/): closing the distance between what leaders say they want and what their systems produce. ## Something in you already knows what needs to go. One email a week that helps you find the thing to stop doing. Subscribe Email sent! Check your inbox to complete your signup. No spam. Unsubscribe anytime. ## The Old Math of Employee Side Hustles For most of my career, side hustles stayed hidden because the math punished them. A role demanded 40 hours of output, a side project consumed 20 more, and something visibly gave. So people built their businesses at night, said nothing at work, and left once the outside thing could support them. The company absorbed the departure and learned nothing. The instinct to build has meanwhile stayed durable. [Bankrate's 2025 survey](https://www.bankrate.com/loans/small-business/side-hustles-survey/?ref=ridiculouslyefficient.com) found 27% of U.S. adults run a side hustle even in a strong job market. Your best people are disproportionately represented in that number, because the same drive that makes them excellent in their role goes looking for its own canvas after hours. The evidence that this helps employers has been sitting in plain sight, too. An [Academy of Management Journal study](https://business.unl.edu/do-hustle-empowerment-side-hustles-and-its-effects-full-time-work-performance?ref=ridiculouslyefficient.com) of 337 employees found that the psychological empowerment people draw from side hustles enriches their full-time work performance. Google wrote a version of this into its culture two decades ago with the [20% rule](https://www.cnbc.com/2021/12/16/google-20-percent-rule-shows-exactly-how-much-time-you-should-spend-learning-new-skills.html?ref=ridiculouslyefficient.com), a standing invitation for employees to spend a slice of their week on projects they believed would most benefit the company. A [handful of companies](https://www.cnbc.com/2021/12/22/these-companies-actually-encourage-staff-to-have-side-hustles.html?ref=ridiculouslyefficient.com) publicly encouraged staff side businesses years before generative AI arrived. Those were the outliers. The default posture held: guard the hours, and treat outside building as leakage. ## The Compression That Broke the 40-Hour Logic AI compressed the time footprint of skilled work, and the compression broke the zero-sum frame. In the old days, if you had 40 hours' worth of work to do, spending 40 hours on a side hustle or a startup was folly to the business. Today everything's compressed. When a week's output fits inside a fraction of the week, hours stop being the scarce resource worth guarding. Capability becomes the scarce resource, and a side hustle is a capability factory the business never has to fund. Stephen Covey named the discipline of stepping back to renew your tools [sharpening the saw](https://www.franklincovey.com/habit-7/?ref=ridiculouslyefficient.com). In the age of AI, you really can sharpen the saw, and the best way to sharpen it is by pursuing something outside your core focus. A side project lets someone nourish themselves in areas where they've been malnourished, without hurting the core business. It's very linear to think people should only ever be working on "the work." The market has already priced in what those saw-sharpening hours produce. [PwC's 2025 Global AI Jobs Barometer](https://www.pwc.com/gx/en/news-room/press-releases/2025/ai-linked-to-a-fourfold-increase-in-productivity-growth.html?ref=ridiculouslyefficient.com) found that jobs requiring AI skills carry a 56% wage premium over comparable roles, up from 25% a year earlier. [Microsoft and LinkedIn's Work Trend Index](https://news.microsoft.com/source/2024/05/08/microsoft-and-linkedin-release-the-2024-work-trend-index-on-the-state-of-ai-at-work/?ref=ridiculouslyefficient.com) found 66% of leaders wouldn't hire someone without AI skills. In [Microsoft's 2025 follow-up](https://www.microsoft.com/en-us/worklab/work-trend-index/2025-the-year-the-frontier-firm-is-born?ref=ridiculouslyefficient.com), 47% of leaders named upskilling existing employees a top workforce strategy. Companies budget for AI training programs while the most motivated training program available walks in the door as somebody's weekend project. ## What Authorization Sounds Like From the Top The variable that decides whether side hustles feed a company or hollow it is the stance of the core decision-maker. My co-founder and CEO of the business set ours in public. A month before that all-hands, he'd turned the previous one into a working session and gotten these tools running on every laptop in the company. Then he encouraged the whole team to build with them, on our own projects, and offered his personal help to anyone who started. He also put a number on his own week, in the same open spirit: roughly $1,200 in AI tokens, producing output he valued in the range of $300,000 of labor equivalence. He offered it as his own back-of-the-envelope math, and the direction matters more than the decimals. Token spend is starting to behave like a unit of labor, and a leader who spends it on his own experiments understands what his team is learning to do. I'm leaving his name out deliberately, because the point is the stance. Any core decision-maker can hold it. A leader responding from scarcity counts the hours a side project consumes. A leader responding from abundance counts the capabilities it returns, then goes first so the team knows the invitation is real. Authorizing, out loud, with help attached: that's the whole move. The fear it replaces (that every skill gained is a step out the door) quietly ran the old policy, and it produced teams that hid their growth from the person best positioned to invest in it. ## What the Side Hustle Sends Back to the Business The fluency someone gains building their own thing comes back into their role through everything they touch. Our salesperson's cold-email instincts sharpened across 86 sends he designed himself. My content system's architecture became frameworks I now apply directly to the systems we build for clients. A weekend project becomes a client win, and a client win becomes a playbook the whole team copies. The alternative to openness has a name now. Microsoft's research found [78% of AI users bring their own tools to work](https://news.microsoft.com/source/2024/05/08/microsoft-and-linkedin-release-the-2024-work-trend-index-on-the-state-of-ai-at-work/?ref=ridiculouslyefficient.com) without waiting for permission. The building happens either way. The only question a leader controls is whether it happens in the open, where the skills get shared at all-hands, or in the shadows, where they compound toward an exit. The retention math favors the open version. [LinkedIn's 2025 Workplace Learning Report](https://www.linkedin.com/business/talent/blog/learning-and-development/2025-workplace-learning-report?ref=ridiculouslyefficient.com) found 88% of organizations worry about retention, and providing learning opportunities is their top strategy for keeping people. A side hustle that generates sovereign income changes what showing up means: once people can afford to leave, you've got to create a reason for them to stay, and the teams that clear that bar hold their absolute aces. Everybody's there by choice. That was the room I was sitting in, and it had a different quality of attention than any team I've been part of. [Every past version of you is source material now](https://www.ridiculouslyefficient.com/every-past-version-of-you-is-source-material-now/), and the same is true of every person on your payroll; some of them are quietly one experiment away from [their first fractional year](https://www.ridiculouslyefficient.com/your-first-year-going-fractional/), and they'll remember who cheered. ## The One Good Thing Test You can run the diagnostic at your next all-hands. Open the meeting by going around the room for one genuinely good thing per person, personal or professional, and say out loud that things built on the side count. Then watch what surfaces. Shares full of experiments mean your team already trusts you with their growth. A quiet room is data of a different kind: your best people may be building anyway, at night, with the door closed. The ritual costs 15 minutes a month, and it tells you which company you're running. What would your best people build if they believed you wanted to hear about it? **Ready to trade scarcity habits for abundant ones?** The Simplicity Protocol helps ambitious professionals do less to achieve more through weekly elimination strategies you can implement in 20 minutes or less. Subscribe and get one idea every Tuesday for building a business, and a life, that runs on abundance. ## Frequently Asked Questions ### Should companies encourage employee side hustles? In the AI era, yes, with clear conflict-of-interest boundaries. The skills employees gain building their own projects, especially AI fluency, return to the organization through everything else they do. Research in the Academy of Management Journal links side-hustle empowerment to stronger full-time performance, and the wage market now prices AI skills at a 56% premium. ### Do side hustles make employees better at their jobs? The Academy of Management Journal study of 337 employees found the psychological empowerment from side hustles enriches full-time performance, with engagement and positive mood carrying over into the day job. Motivating projects produce the strongest effect. ### What if the side hustle competes with the core business? Set the boundary explicitly: outside projects can't serve your clients or draw on confidential work. Most side hustles live far from the core business, and a culture of open sharing surfaces potential conflicts months earlier than a moonlighting policy buried in a handbook. ### How does a leader build AI fluency across a team? Go first, then authorize. Run a hands-on setup session so the tools land on every laptop before enthusiasm cools, and encourage personal experiments outside the core work. Then build a recurring forum where wins get shared in front of everyone. Fluency spreads through demonstrated results faster than through any training curriculum, because a colleague's $6,000 experiment is proof in a way no slide deck can be. ### Won't people leave once their side income grows? People with options stay for reasons deeper than a paycheck. Helping your team build sovereign income raises the bar your culture has to clear, and leaders who clear it keep their aces by choice. Alumni who launch send business back. ## One nonessential to eliminate before next week. One insight every Tuesday for ambitious professionals navigating major transitions. Five-minute read. Subscribe Email sent! Check your inbox to complete your signup. No spam. Unsubscribe anytime. ## Sources - [Microsoft and LinkedIn 2024 Work Trend Index](https://news.microsoft.com/source/2024/05/08/microsoft-and-linkedin-release-the-2024-work-trend-index-on-the-state-of-ai-at-work/?ref=ridiculouslyefficient.com) - [Sessions et al., "Do the Hustle!" Academy of Management Journal](https://business.unl.edu/do-hustle-empowerment-side-hustles-and-its-effects-full-time-work-performance?ref=ridiculouslyefficient.com) - [Bankrate 2025 Side Hustle Survey](https://www.bankrate.com/loans/small-business/side-hustles-survey/?ref=ridiculouslyefficient.com) - [PwC 2025 Global AI Jobs Barometer](https://www.pwc.com/gx/en/news-room/press-releases/2025/ai-linked-to-a-fourfold-increase-in-productivity-growth.html?ref=ridiculouslyefficient.com) - [Microsoft 2025 Work Trend Index: The Year the Frontier Firm Is Born](https://www.microsoft.com/en-us/worklab/work-trend-index/2025-the-year-the-frontier-firm-is-born?ref=ridiculouslyefficient.com) - [LinkedIn 2025 Workplace Learning Report](https://www.linkedin.com/business/talent/blog/learning-and-development/2025-workplace-learning-report?ref=ridiculouslyefficient.com) - [FranklinCovey, Habit 7: Sharpen the Saw](https://www.franklincovey.com/habit-7/?ref=ridiculouslyefficient.com) - [CNBC: Meet the companies encouraging side hustles](https://www.cnbc.com/2021/12/22/these-companies-actually-encourage-staff-to-have-side-hustles.html?ref=ridiculouslyefficient.com) - [CNBC: Google's 20% rule](https://www.cnbc.com/2021/12/16/google-20-percent-rule-shows-exactly-how-much-time-you-should-spend-learning-new-skills.html?ref=ridiculouslyefficient.com)