#862 The Two-Week Startup
Brian O'Connor spent three years building a 40,000-person Twitter following, launched product after product into that audience, and made almost nothing. The turning point came when he stopped looking for clever ideas and...
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#861 One Niche, One Funnel, Over $50K/Month Profit
At his lowest point, Jan Roos was $240,000 underwater. He had a full sales org, a director, reps, ad spend — and was barely breaking even. So he cut all of it. Today he runs CaseFuel, a high-margin agency serving 300+ es...
#860 How Direct Mail Built a Multi-Million Dollar Business
Robert Dow buys and sells raw land across Texas and Oklahoma — mostly sight unseen, almost entirely through direct mail. It's a lean operation built on a simple idea: take infrastructure you already have and point it at ...
#859 Building a $6.5M Remote Agency in 5 Years — LevelUp Leads
Dan interviews John Karsant, founder of Level Up Leads, a 73-person outsourced SDR agency doing about $6.5M/year revenue, built while living abroad (Argentina, now Barcelona). John shares how he found remote work early v...
#858 Paying for Growth in 2026
Is 2026 the year you finally run paid ads? Something shifted at DC Mexico this year — more founders than ever are seriously considering paid ads as their next acquisition channel. Between AI making creative cheaper to pr...
#857 AI and the High-Margin Agency: What's Working in 2026
Dan and Ian are joined by Jeff Picaro of meetwingman.com to recap lessons from the DC Mexico event and share five trends for 2026 in bootstrapped, location-independent businesses. In this episode: • Why organic traffic...
#856 "Trust is the New Currency" — Hot Takes from 200 Founders in Mexico City
Dan and Ian just got back from DC Mexico — 4 days in Mexico City with 200 founders, a third of whom run $1M+ businesses. Three ideas worth sitting with: Reading about something is useful. Watching someone implement it is...
#855 Hard Questions, Easy Business
Most founders already know what's wrong with their business. The fix is usually simple but scary. So instead of doing the one hard thing that would make everything else easier, they stay busy. It feels like progress. It ...
#854 5 Simple Ways Agencies Are Using AI
Dan and Jeff Pecaro (meetwingman.com) share five practical ways agency founders are using AI right now—sharpening positioning, analyzing sales calls, rebuilding websites, testing offers, and creating content faster. They...
#853 AI Is Useful. Now What?
Dan and Ian break down the real use cases they’re seeing inside DC companies right now — not theory, not hype, but the actual workflows founders are using to make and save money. They cover: ● The difference between side...
#852 I Wasted $40K on an AI Agency. Here's What I Built Instead
Aaron Anderson runs a link building agency — 8 years in, fully remote, team of 10. A year ago, his business was in negative growth. He decided to go all-in on AI and hired an agency to rebuild his systems. He paid them n...
#851 $1,000,000+ Recurring Revenue — No Employees!
Most founders assume scaling means hiring. Jesse Hanley built a 7-figure SaaS and refused to. From Japan, Jesse runs Bento — a profitable email marketing platform — almost entirely on his own. In this episode, he explain...
#850 We Got Claude-Pilled
After a week of going all-in with Claude and agentic AI, Dan and Ian share what happened when they plugged AI directly into their company workflows. What followed felt less like using software — and more like jockeying a...
#849 Advanced Personal Finance for Entrepreneurs
We're often great at making money, terrible at managing it. Multi-exit entrepreneur David McKeegan joins us to discuss personal finance built specifically for founders: The "refrigerator number" — what it is and how to ...
#848 The $10K Projects You Never Do (AI Just Changed That)
Dan talks with Taylor Pearson about a new wave of “agentic AI” tools like Claude Code — and how founders are using them to tackle projects that used to take days or weeks. From analyzing financials to running workflows a...
#847 From Semi-Retired to 1.3 Million Views on YouTube ft. Richard “RJ” Jalichandra
A semi-retired 6-time CEO accidentally went viral on YouTube, and turned it into a real business case study. Dynamite Circle member and DC BLACK facilitator, Richard “RJ” Jalichandra, joins us this week to talk about how...
#846 Can Your Business Beat the S&P 500?
Dan and Ian hop on the mic to talk about spending money to make more money in your business, getting financial assistance with AI, how to decide where you should live and work in 2026, and agentic AI use cases. Meet life...
#845 How to Build a 6-Figure Digital Business with Claude Code
How long would it take to revamp your entire business? For Elliott Zelinskas: three weeks. Using Claude Code, he rebuilt his 4-year website, generated 100+ SEO pages, automated YouTube creation and publishing, and replac...
#844 4 Ways to Start a Business From Scratch in 2026
Dan and Ian respond to a listener's email about strategies for going from a 9-5 to full-blown entrepreneurship, and why mindset is far more important long-term than ideas if you want to start a business. LINKS Bento will...
#843 Bad Hiring Advice That Can Actually Work: 9 Tactics for Lifestyle Founders
Dan and Ian share 9 pieces of hiring advice that are typically considered “bad,” but can actually work pretty well for smaller bootstrapped teams - and especially lifestyle businesses. LINKS Bento will beat your current ...