#824 The Outsourcing Shake-Up: LATAM vs. Philippines
11 Sep 2025
Contributed by Lukas
It’s another mixed bag of business topics on this week’s episode of the pod: X’s Head of Produ...
#823 Why $120K From Your Biz Beats $150K at a Job
04 Sep 2025
Contributed by Lukas
Why are so many chasing $10M exits when $3-4M plus a paid-off house might be the real freedom number...
#822 5 Bootstrapper Takeaways from Hormozi’s $100M Launch
28 Aug 2025
Contributed by Lukas
If you’ve been living under a rock, you might have missed Alex Hormozi’s record-breaking launch ...
#821 $400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton
21 Aug 2025
Contributed by Lukas
In this week’s episode, Allen Walton (SpyGuy) shares how he’s using AI to build custom tools wit...
#820 Top 5 SEO Tactics That Still Work in 2025 with Sean Markey
14 Aug 2025
Contributed by Lukas
Organic traffic is getting weird… and kinda looks like an alligator’s mouth (you’ll have to li...
#819 Why Founders Shouldn’t Delegate AI (Barcelona Recap)
07 Aug 2025
Contributed by Lukas
How are legit 7- and 8-figure founders leveraging AI in their businesses? Spoiler alert: they’re n...
#818 The Content Flywheel Behind a 7-Figure Education Business ft. Timothy Moser
31 Jul 2025
Contributed by Lukas
Timothy Moser, founder of LearnCraft Spanish, shares how he scaled a 7-figure education business in ...
#817 Health Advice That Goes Against Everything You Know ft. Jay Feldman
24 Jul 2025
Contributed by Lukas
When Dan started training for an intense cycling season, he needed more energy... without wrecking h...
#816 Reddit Hot Takes on Entrepreneurship: Founders React
17 Jul 2025
Contributed by Lukas
Dan and Ian respond to a series of spicy "unpopular opinions" about entrepreneurship, employment, di...
#815 Zero-Profit Events, CFO Swaps, and LATAM Talent: 2025 Halftime Report
10 Jul 2025
Contributed by Lukas
We’re halfway through 2025! This episode is a raw look at what’s working, what’s not, and the ...
#814 Growth vs. Optimization — 90% of Growth Comes from 10% of Activities?
03 Jul 2025
Contributed by Lukas
What happens when you’ve optimized everything… and growth still stalls? In this episode, Dan and...
#813 7-Figure Marketing with Zero Ad Spend ft. Karla Singson
26 Jun 2025
Contributed by Lukas
What marketing strategies are actually working in 2025? Karla Singson shares standout tactics from a...
#812 From Struggling Plumber to $57K MRR w/ Tom Richards
19 Jun 2025
Contributed by Lukas
From hating life on a Sydney construction site to building a $57K/month agency from Bali, Tom Richar...
#811 The Brutal Truth About Business Exits with Rob Walling
12 Jun 2025
Contributed by Lukas
Thinking of selling your business one day? Or never planning to? Either way, this conversation could...
#810 The Lifestyle Business Playbook (2025 Edition)
05 Jun 2025
Contributed by Lukas
Is the “lifestyle business” still alive in 2025? Dan chats with longtime friend Jeff Pecaro abou...
#809 Financial Traps, Profit Truths, and What’s Next at TMBA
29 May 2025
Contributed by Lukas
Many founders hit $3M in revenue and stall out. In this episode, Dan and Greg Crabtree break down wh...
#808 Going Deep With Your Customers
22 May 2025
Contributed by Lukas
What 160 founders taught us at DC Mexico—why deep customer engagement beats ads, how group worksho...
#807 Location is Leverage
15 May 2025
Contributed by Lukas
Dan shares how advanced digital nomads use geography as a lever for business growth—and why most p...
#806 50/50 Partnerships: Saying the Quiet Part Out Loud
08 May 2025
Contributed by Lukas
Dan shares why most bootstrapped business partnerships go sideways—and what to do if yours already...
#805 What Every Profitable Business Gets Right
01 May 2025
Contributed by Lukas
This week, Dan goes back to the basics—because that’s where the breakthroughs often live. This m...
#804 Marketing to High-Dollar Clients
24 Apr 2025
Contributed by Lukas
Dan shares a relationship-first strategy for landing bigger deals—no funnels, no ads, just a focus...
#803 I Can’t Stick With It. Should I?
17 Apr 2025
Contributed by Lukas
What if your struggle to follow through isn’t a discipline problem — but a signal? This week, Da...
#802 The 10 Behaviors Killing Your Business — Masked as Productivity
10 Apr 2025
Contributed by Lukas
Some of the “smart moves” founders make might be signs of hidden resistance. This week, Dan and ...
#801 Why Founders Stall at $300K + The Blank Sheet
03 Apr 2025
Contributed by Lukas
Dan shares strategies for creating value as an entrepreneur - from maximizing personal productivity ...
#800 Our Lifestyle Business Non-Negotiables
27 Mar 2025
Contributed by Lukas
Dan and Ian break down what makes a great lifestyle business in 2025—one that delivers both strong...
#799 90-Day Growth Plan in 10 Questions
20 Mar 2025
Contributed by Lukas
What if 90 days from now, your business was sharper, more focused, and positioned for real growth? I...
#798 Observations From our Trip to Thailand
13 Mar 2025
Contributed by Lukas
Dan and Ian share key insights from their Thailand mastermind event, exploring how successful entrep...
#797 DOGE, Team Resets & The 1,000-Day Playbook
06 Mar 2025
Contributed by Lukas
Dan unpacks what business owners can adapt from DOGE’s new strategy, delivers a practical cure for...
#796 Bigger Business = More Freedom?
27 Feb 2025
Contributed by Lukas
Dan sits down with Neel Parekh (CEO of MaidThis Franchise) to talk about the shifts that drive real...
Bonus Pod: Inside the DC in 2025
25 Feb 2025
Contributed by Lukas
The team takes you inside the DC. Who we are, what to expect, and how you can grow your business wit...
#795 "The Tailwind Index" & Dodging Business Blindspots
20 Feb 2025
Contributed by Lukas
The stories we tell ourselves shape our businesses—but how much of it is true? External validation...
#794 Success Without Sacrifice?
13 Feb 2025
Contributed by Lukas
Dan breaks down five key mindset shifts for business owners in the thick of the growth grind. Inspir...
#793 The Unexpected Downsides of Selling Your Business
06 Feb 2025
Contributed by Lukas
Why do so many founders feel sad, lost, and even depressed when they come into life-changing money f...
#792 Is SEO Dead?
30 Jan 2025
Contributed by Lukas
Dan discusses the shift in SEO and the decline of content sites, emphasizing the need for B2B niche ...
#791 Is Your Biggest Expense Helping or Hurting?
23 Jan 2025
Contributed by Lukas
One of the first questions Dan asks in his coaching sessions with 6 & 7-figure entrepreneurs is: wou...
#790 The 2024 Recap: Business Updates, Financial Insights & Family Matters
17 Jan 2025
Contributed by Lukas
Dan and Ian reflect on their personal and business highlights from 2024, discussing parenting, trave...
#789 You Already Have a Personal Brand—Here’s How to Make It Work for You
09 Jan 2025
Contributed by Lukas
A personal brand is all about perception—everyone has one, whether you like it or not. So why not ...
#788 Niche B2B Content = Big Revenue on YouTube
02 Jan 2025
Contributed by Lukas
Shane Hummus reveals his proven strategy for turning YouTube into a reliable source of new clients a...
#787 10 Questions to Gain Clarity and Refocus
26 Dec 2024
Contributed by Lukas
Dan and lan break down 10 essential questions to help you reflect on the year, align your priorities...
#786 Jay Clouse - Mastering Top-of-Funnel Growth in 2025
19 Dec 2024
Contributed by Lukas
Dan welcomes back Jay Clouse, founder of Creator Science, for his third appearance on the podcast. J...
#785 Scaling to 8-Figures with Ruthless Focus and Unconventional Principles
12 Dec 2024
Contributed by Lukas
Dan talks to Matthew Newton, CEO of Leatherback Travel, about his radically unconventional approach ...
#784 “$1.5 Million from LinkedIn: Strategies for Building Influence and Consistent Revenue”
05 Dec 2024
Contributed by Lukas
If you’re sleeping on LinkedIn, let this episode be your wake up call. Dan sits down with Dr. Alex...
#783 “It’s easier to 10X than to 2X” + 8 Lessons from CEO Bootcamp
28 Nov 2024
Contributed by Lukas
Dan and Ian traveled to Barcelona with 12 other CEOs and founders to spend the week with Scaling Up ...
#782 Building ‘Brick by Brick’: Goals, Plans, Scorecards, Cadence
21 Nov 2024
Contributed by Lukas
Does your business feel stuck in 'idea mode,' constantly jumping from project to project? If you’r...
#781 “Build It Like You’re Gonna Sell It”
14 Nov 2024
Contributed by Lukas
Dan revives his Re-Readables series with a discussion inspired by Frank Slootman's business book Amp...
#780 How do you grow from 7 to 8 figures?
07 Nov 2024
Contributed by Lukas
Dan & Ian talk to Lucas Peters, founder of Journey Beyond Travel (https://www.journeybeyondtravel.co...
#779 The 3 hats of bootstrapping + Insights from DCBKK 2024
31 Oct 2024
Contributed by Lukas
Dan and Ian discuss the importance of three key executive roles—CEO, COO, and CFO—within bootstr...
#778 - Agencies vs. Products + What Happened in the Amazon Aggregator Space?
24 Oct 2024
Contributed by Lukas
This week’s episode is for the business finance and idea nerds. We’re joined this week in a bus...
#777 Create and Communicate an Offer (That Doesn’t Suck) in 30 Minutes
17 Oct 2024
Contributed by Lukas
Selling your product or service requires using words to convey what you offer. But words alone don’...
#776 The 4 Most Eye-Opening Lessons I’ve Learned From My Coaching Clients
10 Oct 2024
Contributed by Lukas
Dan and Ian talk to 100s of listeners a year via 1:1 coaching. In this episode they distill those ca...
#775 A Business Idea That Might Actually Work
03 Oct 2024
Contributed by Lukas
Dan considers why many of us are resistant to a certain type of business idea even when it’s been ...
#774 “You’re Gonna Mess It Up The Way Everybody Messes It Up”
26 Sep 2024
Contributed by Lukas
Dan paid big money for a business coach who only gave him one piece of advice. Listen to the episode...
#773 6 Keys to a Successful Bootstrapped Business
19 Sep 2024
Contributed by Lukas
Dan & Ian get real about what it takes to create and maintain a successful business. They’ll walk ...
#772 “When is my LTV good enough?” + Founder Mode for Bootstrappers
12 Sep 2024
Contributed by Lukas
“Manager mode is so tempting…” Dan & Ian discuss Paul Graham’s most recent essay titled “F...
#770 You Don’t Have an Operations Problem. You Have a Sales & Marketing Problem.
05 Sep 2024
Contributed by Lukas
Many founders think they have an operations problem - delivery, trust, staffing, leadership. But Dan...
#770 $30K a Month on Upwork in Less Than 2 Years
29 Aug 2024
Contributed by Lukas
This founder started an Upwork agency less than 2 years ago and is making $30K a month… JUST on Up...
#769 - $100K MRR in 12 Months… Can They Do It?
22 Aug 2024
Contributed by Lukas
These co-founders want to more than triple their revenue in the next 12 months. Despite stagnation t...
#768 “Lifestyle Business” vs “Real Business”
15 Aug 2024
Contributed by Lukas
Go from being trapped in the job you’ve built for yourself to building a wealth-generating machine...
#767 “1,000 Customers from One Channel”
08 Aug 2024
Contributed by Lukas
Dan & Ian talk to a listener who’s running a SaaS business that within one year got to $8K MRR. Th...
#766 “I’m Scared to Raise the Price”
01 Aug 2024
Contributed by Lukas
Dan & Ian talk to a listener who’s running a $1M D2C e-commerce business about the challenges and ...
#765 Only 3 Ways to Grow…What Would Plato Do
25 Jul 2024
Contributed by Lukas
Tackling one of the biggest problems entrepreneurs struggle with: separating their business from the...
#764 The 5 Approaches for Getting Rich + Budgeting for Wealth
18 Jul 2024
Contributed by Lukas
We speak to hundreds of entrepreneurs every year through one-on-one coaching and live events. Many ...
#763 10 ideas for businesses seeking $1 Mil in Revenue
11 Jul 2024
Contributed by Lukas
In this week's conversation, Dan and Ian discuss 10 ideas that provide valuable insights and strateg...
#762 Winning and Losing Millions with Nathaniel Eliason
04 Jul 2024
Contributed by Lukas
This week’s conversation revolves around the book 'Crypto Confidential' and explores author Nathan...
#761 - Less Than 5% of Businesses Get to 1MIL+ - A Process to Reach the Goal
27 Jun 2024
Contributed by Lukas
Dan and Ian discuss the fundamental principles of change and how they apply to both weight loss and ...
#760 - The 7 Most Common Money Mistakes for Bootstrappers
20 Jun 2024
Contributed by Lukas
Dan and Ian discuss the biggest money problems they’ve seen in their own business and hundreds of ...
#759 - Unlock Wealth Through Financial Fluency
13 Jun 2024
Contributed by Lukas
In this episode, Dan and Ian discuss the credible and reliable ways to build wealth through your bus...
#758 - The Secret Weapon to Pricing Power
06 Jun 2024
Contributed by Lukas
Dan and Ian explore the concept of power in business and how businesses can transition from being a ...
#757 - How Healthy is Your Business?
30 May 2024
Contributed by Lukas
Dan and Ian challenge listeners to answer five questions about your business that will help you eval...
#756 - The Million Dollar Service Business Playbook
23 May 2024
Contributed by Lukas
In this week's episode Dan and Ian discuss the importance of the concept of Labor Efficiency Ratio (...
#755 - Run Any Business With Just Two Simple Things
16 May 2024
Contributed by Lukas
Dan reflects on his trip to Mexico last week where he hung out with 200 founders and listeners of th...
#754 - Mastering Consistency with Adam Gilbert
09 May 2024
Contributed by Lukas
Health and wellness is the ultimate productivity hack, impacting every aspect of life. Adam Gilbert...
Lessons From an 18-Month Trip Around the World on $100 a Day
02 May 2024
Contributed by Lukas
This week we had the pleasure of sitting down with Barry O'Brien, a global traveler, as he shares hi...
#752 The 1 Million Dollar Question
25 Apr 2024
Contributed by Lukas
Crafting your value proposition into an irresistible offer is not an easy task. Andrew Jacoby, entre...
#751 “The Death of the Follower” + How I’d Make $250K in 3 Days a Week
18 Apr 2024
Contributed by Lukas
Is it possible to bootstrap a high-level business if you’re broke? Listen to Dan & Ian’s take on...
#750 What is the Most Simple OS for <$5M?
11 Apr 2024
Contributed by Lukas
The hard part shouldn’t be how to implement an OS in your organization. The hard part is answering...
#749 Do Things That Don’t Scale
04 Apr 2024
Contributed by Lukas
In this episode, Ian and Dan discuss the concept of doing things that don't scale, inspired by Paul ...
#748 Three Phases to 1 Million
28 Mar 2024
Contributed by Lukas
Dan and Ian discuss the different phases of bootstrapping a business and the common challenges that ...
#747 Quiet Crypto, The Demand Question, and Difficult Decisions ft. Jordan Gal
21 Mar 2024
Contributed by Lukas
Dan talks to Jordan Gal, founder of Rally and co-host of the Bootsrapped Web podcast about challenge...
#746 “Full-Service Agencies Are Out” & Other Productized-Service Ideas
14 Mar 2024
Contributed by Lukas
Dan & Ian talk to John Doherty, the founder of Editor Ninja, former owner of Credo, and cohost of th...
#745 “3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree
07 Mar 2024
Contributed by Lukas
Transitioning through the death zone requires careful execution and a focus on profitability. The $3...
#744 How Transparent Should You Be? Thoughts on Queen Bee Roles & a Ticket Giveaway
29 Feb 2024
Contributed by Lukas
This week Dan & Ian share a few thought experiments you can do to improve your business and reach yo...
#743 Spotting Taboo Business Ideas Through the Overton Window
22 Feb 2024
Contributed by Lukas
Going deeper on shiny object syndrome, Dan & Ian open the mailbag to read responses to last week’s...
#742 A Podcast About Shiny Object Syndrome
15 Feb 2024
Contributed by Lukas
Dan & Ian delve into the complexities of combating shiny object syndrome, a challenge that plagues a...
#741 The Roadmap for Turning a Skill Into a 1M+ Productized Service
08 Feb 2024
Contributed by Lukas
In this episode Dan uncovers The Ultimate TMBA Business: a productized service business built on a s...
#740 The Anti-Agency Agency + High ROI Customer Acquisition
01 Feb 2024
Contributed by Lukas
Vince Nguyen joins Dan to share how he resurrected his agency from semi-retirement and in the first ...
#739 The Three Horsemen Holding Your Business Back from Breakthrough with Mike Michalowicz
25 Jan 2024
Contributed by Lukas
Dan interviews business author and entrepreneur Mike Michalowicz, delving into the transformative co...
#738 Under the Hood of an 8-Figure Business + Million Dollar Weekend with Noah Kagan
18 Jan 2024
Contributed by Lukas
“Noah’s new book Million Dollar Weekend has so many nuggets for aspiring and mature entrepreneur...
#737 Business Basics: Revenue Durability, “Small” Goals, & High-Leverage Meetings
11 Jan 2024
Contributed by Lukas
Today Dan & Ian challenge you to consider: How durable is your revenue? They’ll explore the concep...
#736 How to Have Your Best Year $$$Wise Ever
04 Jan 2024
Contributed by Lukas
This week, Dan reveals a strategic approach to decision-making intervals for achieving top-line reve...
#735 An 8-figure exit and revisiting the 1,000-day principle
28 Dec 2023
Contributed by Lukas
Can you make a life-changing decision based on assumptions you pulled off the internet? This questio...
#734 Non-Obvious Ways to Grow Your Business + Favorite Moments of 2023
21 Dec 2023
Contributed by Lukas
As 2023 comes to a close, Dan & Ian reflect on how their business did in 2023 and share some of thei...
#733 End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown
14 Dec 2023
Contributed by Lukas
Dan & Ian offer up some end-of-year thought experiments for founders, including how to re-visualize ...
#732 Can Org Charts Be Sexy? + NYC Drinking Stories
07 Dec 2023
Contributed by Lukas
Dan & Ian unravel the complexities of job titles and organizational frustrations post-DC Black event...
#731 Special Edition Pod: Meet us in Mexico
05 Dec 2023
Contributed by Lukas
In this special Tuesday edition of the pod, Dan & Ian make the hard sell for listeners to meet them ...
#730 Cash Flowing Your Early Retirement (10K/mo+)
30 Nov 2023
Contributed by Lukas
This week, Dan continues delving into the world of coaching with a story about one company that prov...
#729 What is the Michael Jordan of Business Models?
23 Nov 2023
Contributed by Lukas
All we can say is that it’s extremely powerful and extremely profitable. Dan and Ian nerd out on w...
#728 Mailbag: Hang-ups, Power-ups, and Cheat Codes for Entrepreneurs
16 Nov 2023
Contributed by Lukas
Dan & Ian open up the metaphorical mailbag to answer some listener questions. They reveal cheat code...
#727 The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap
09 Nov 2023
Contributed by Lukas
This week Dan & Ian talk about a topic that came up countless times at this year’s DCBKK: Whether ...
#726 Insights from DCBKK 2023: The UI vs API of a Location, How Bootstrappers Are Getting Wealthy, 2024 Business Strategy, and More
02 Nov 2023
Contributed by Lukas
Dan & Ian are back in Austin and have fully recovered from what was the biggest event in DC history:...