21 Hats Podcast

A lot of business owners are taking a wait-and-see approach with artificial intelligence. They’ve heard the hype—but they’ve also heard about the slop, the hallucinations, and the research suggesting many AI projects fail to deliver. For plenty of owners, that’s reason enough to assume this might be another passing obsession—like Y2K, Clubhouse, or the metaverse—and to sit back until the dust settles.But not these three owners: David C. Barnett, Jaci Russo, and William Vanderbloemen have decided that waiting is the bigger risk. They’re taking courses, they’re teaching courses, they’re building agents, and they’re rethinking processes and workflows—all in search of an edge that may not be available forever. And they’re already seeing results.In this episode, they share what’s actually working so far, including some early experiments that could reduce their reliance on Google AdWords. They also talk candidly about what they won’t do with AI, how they sidestep the slop, and why each of them believes this is one of those rare moments when experimentation isn’t optional.

Yes, says Gene Marks in this week’s Dashboard, the Supreme Court’s tariff decision, while correct, has created a mess. No, you shouldn’t make any plans to spend your tariff refund money. And no, there’s no telling where the Trump administration might be heading. But he does offer this one shred of certainty: For many businesses that have been paying the so-called reciprocal tariffs, if they plan for a 15-percent tariff rate going forward, they’ll probably be in reasonably safe territory.

Sonali Kothari, co-founder of Zolidar and former Kiva.org tech and social impact leader, builds tools to help small and medium business owners explore exit and succession options. She discusses unbiased comparisons of sale types, employee ownership and ESOPs, Zolidar’s Day Zero Guide, AI co-pilot transparency, and scaling affordable exit planning for many businesses.

Ted Wolf, CEO of GuideWise, tech builder turned AI implementer. Jackie Russo, CEO of Brand Russo, agency leader and branding strategist. Kate Morgan, CEO of Boston Human Capital Partners, recruiter and fractional HR pro. They riff on hiring and talent readiness. They swap worst-job stories and resilience lessons. They debate crypto, smart ways to spend $10,000 on marketing, and whether agencies should hire other agencies.

Kelly Berry, facilitator of peer groups for business owners and founder of Second Stage Growth, helps rural and small firms scale. She talks about why peer groups work, how they create accountability and safe spaces for hard conversations, and the strategies she uses to bring virtual support to owners who lack local resources.

Jackie Russo, marketing CEO focused on AI/SEO-friendly websites and audience targeting. Paul Downs, custom furniture maker who uses portfolio and pricing strategies to qualify buyers. Liz Piccarazzi, CEO scaling a multi-million trash enclosure business rebuilding her site and ops. They talk website rebuilds, tailoring paths for multiple audiences, SEO/AI content needs, pricing transparency, and operational scaling pains.

Gary Kunkel, an economist who researches sustained growth and why few firms create most jobs. He discusses the 1% growth pattern, the customer profitability "whale" where ~20% drive profits, risks of fast growth and debt, and the 50 decisions and six drivers that enable repeatable, disciplined scaling. Practical steps for diagnosing unprofitable customers and prioritizing durable growth are highlighted.

Alan Pence, a consultant who helps small business owners adopt AI, warns a major disruption is coming and wrestles with whether owners want help. He explores why adoption lags, which knowledge-work industries are most exposed, and different business models from training implementers to AI-savvy VAs. The conversation probes messaging, scalability, and what proof would convince him to build this service.

Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly because it offers a practical, step-by-step playbook that helps owners think through pricing, staffing, cash flow, and growth decisions, using AI to guide—not replace—their judgment. This week on Dashboard, Ryan walks us through what happens when one industry gets an AI playbook for running a business—and why landscaping may be an early glimpse of what’s coming for a lot of small business owners.

Shannon Kennedy, founder of Kiwi Vision and maker of the Morgan Square tool; Jackie Russo, CEO of Brand Russo and Profit First adopter; Sarah Siegel, CEO of Siegel Communications navigating rapid growth. They debate hiring before revenue arrives, temp-to-perm and junior-first hiring tactics, balancing office culture with hybrid work, practical AI use, and Profit First budgeting shifts.