This week's episode is full of actionable advice for anyone who is looking to improve their revenue and optimize their sales.We were taking notes throughout the entire conversation with today's guest, and by the time it had ended, it felt like

#752 The 1 Million Dollar Question

5 days ago 45m 15s

Crafting your value proposition into an irresistible offer is not an easy task. Andrew Jacoby, entrepreneur and visionary behind Growth Era, a thriving outbound sales company, knows this all too well. Andrew shares his journey, highlighting th

#751 “The Death of the Follower” + How I’d Make $250K in 3 Days a Week

12 days ago 34m 1s

Is it possible to bootstrap a high-level business if you’re broke? Listen to Dan & Ian’s take on what kinds of businesses are best to start when you’re starting with basically nothing. Also, what the hell does a visionary do? Dan suggests that

#750 What is the Most Simple OS for <$5M?

19 days ago 30m 58s

The hard part shouldn’t be how to implement an OS in your organization. The hard part is answering the question: Are the right people in the right roles at your company? In this episode, Dan and Ian share their own OS that’s extremely simple.

#749 Do Things That Don’t Scale

26 days ago 47m 4s

In this episode, Ian and Dan discuss the concept of doing things that don't scale, inspired by Paul Graham's influential article 'Do Things That Don't Scale.' They explore the idea of taking risks and gambling in entrepreneurship, and how it re

#748 Three Phases to 1 Million

Mar 28th, 2024 42m 23s

Dan and Ian discuss the different phases of bootstrapping a business and the common challenges that arise at each stage. They walk through three phases: Zero to $250k “Mindset”; $250k to 1 million "We're seeking a reliable/repeatable source of

#747 Quiet Crypto, The Demand Question, and Difficult Decisions ft. Jordan Gal

Mar 21st, 2024 1h 1m

Dan talks to Jordan Gal, founder of Rally and co-host of the Bootsrapped Web podcast about challenges in the ecommerce space, product-market fit and demand, partnerships and veto power, the quietness of crypto, risking other people’s money, and

#746 “Full-Service Agencies Are Out” & Other Productized-Service Ideas

Mar 14th, 2024 54m 19s

Dan & Ian talk to John Doherty, the founder of Editor Ninja, former owner of Credo, and cohost of the Working Sessions podcast about three major trends he’s seeing in the agency space that could impact your strategy and profitability for the ye

#745 “3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree

Mar 7th, 2024 44m 52s

Transitioning through the death zone requires careful execution and a focus on profitability. The $3 million dollar mark is a critical milestone for businesses, and many struggle to push through it.In this episode, Dan talks to Greg Crabtree,

#744 How Transparent Should You Be? Thoughts on Queen Bee Roles & a Ticket Giveaway

Feb 29th, 2024 41m 51s

This week Dan & Ian share a few thought experiments you can do to improve your business and reach your next breakthrough. They cover the value of a writing-first culture, the Queen Bee Role & how transparent should you be with your team?Plus,

#743 Spotting Taboo Business Ideas Through the Overton Window

Feb 22nd, 2024 53m 34s

Going deeper on shiny object syndrome, Dan & Ian open the mailbag to read responses to last week’s episode. A listener shares his success story with shiny object syndrome, revealing how he pursues his entrepreneurial impulses without growing cr

#742 A Podcast About Shiny Object Syndrome

Feb 15th, 2024 1h 4m

Dan & Ian delve into the complexities of combating shiny object syndrome, a challenge that plagues all entrepreneurs at one time or another (or all the time). They’ll talk about six strategies for tackling “the syndrome” and how to harness you

#741 The Roadmap for Turning a Skill Into a 1M+ Productized Service

Feb 8th, 2024 47m 43s

In this episode Dan uncovers The Ultimate TMBA Business: a productized service business built on a skill set. Tom Kent started his business based on a very specific skill set of his: he was good at getting jobs. Now Tom is the founder and CEO

#740 The Anti-Agency Agency + High ROI Customer Acquisition

Feb 1st, 2024 1h 26m

Vince Nguyen joins Dan to share how he resurrected his agency from semi-retirement and in the first month resumed making 5+ figures per client. He runs his agency solo and shares some of his biggest hacks for success. Vince essentially delivers

#739 The Three Horsemen Holding Your Business Back from Breakthrough with Mike Michalowicz

Jan 25th, 2024 51m 22s

Dan interviews business author and entrepreneur Mike Michalowicz, delving into the transformative concepts from Mike's books — "Profit First," "The Pumpkin Plan," Clockwork", and more. They explore the power of prioritizing profit and why most

#738 Under the Hood of an 8-Figure Business + Million Dollar Weekend with Noah Kagan

Jan 18th, 2024 35m 19s

“Noah’s new book Million Dollar Weekend has so many nuggets for aspiring and mature entrepreneurs alike. Specifically, if you’re launching a new product, starting a new business, or you want to keep things simple for your team, you’ll find tang

#737 Business Basics: Revenue Durability, “Small” Goals, & High-Leverage Meetings

Jan 11th, 2024 33m 39s

Today Dan & Ian challenge you to consider: How durable is your revenue?They’ll explore the concepts of profit now vs profit later, investing profits to build durability, network effects, marginal profitability calculation, and more. But first

#736 How to Have Your Best Year $$$Wise Ever

Jan 4th, 2024 33m 23s

This week, Dan reveals a strategic approach to decision-making intervals for achieving top-line revenue and personal income goals. Join him as he explores how this decision-making cadence serves as a compass in navigating the challenging 'messy

#735 An 8-figure exit and revisiting the 1,000-day principle

Dec 28th, 2023 51m 30s

Can you make a life-changing decision based on assumptions you pulled off the internet?This question and many others are answered in today’s fascinating interview with two of Dan’s mentors and longtime friends.They recently exited one of thei

#734 Non-Obvious Ways to Grow Your Business + Favorite Moments of 2023

Dec 21st, 2023 56m 28s

As 2023 comes to a close, Dan & Ian reflect on how their business did in 2023 and share some of their favorite moments from the year. They’ll also talk about what makes a compelling offer, the “non-obvious ways” to grow your business in 2024,

#733 End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown

Dec 14th, 2023 36m 52s

Dan & Ian offer up some end-of-year thought experiments for founders, including how to re-visualize your business, capitalize on strategy, and ensure that you are in the right role in your business. Most founders assume they are the “executive

#732 Can Org Charts Be Sexy? + NYC Drinking Stories

Dec 7th, 2023 40m 19s

Dan & Ian unravel the complexities of job titles and organizational frustrations post-DC Black event, offering solutions through org chart brainstorming, a new business idea, and how much you should be investing into networking strategies based

#731 Special Edition Pod: Meet us in Mexico

Dec 5th, 2023 9m

In this special Tuesday edition of the pod, Dan & Ian make the hard sell for listeners to meet them in Mexico.If you’re into five-star resorts, good food, frosty drinks, and nerding out about your business, consider this your official invite.

#730 Cash Flowing Your Early Retirement (10K/mo+)

Nov 30th, 2023 45m 18s

This week, Dan continues delving into the world of coaching with a story about one company that provides highly paid professionals with a low-stress way to earn a living in the sunset phase of their careers. Dan also interviews Sarah Weaver, a

#729 What is the Michael Jordan of Business Models?

Nov 23rd, 2023 44m 12s

All we can say is that it’s extremely powerful and extremely profitable. Dan and Ian nerd out on what might be the GOAT business model of all time. They analyze some of the best examples of said business model, and talk about ways that you can