5 Best Rob Walling Podcasts in 2026

1. How to Leverage AI to 5x Your Impact

Follow Play Jun 30, 2025 27:14
Website Apple Spotify YouTube
About Episode Rob Walling, Tinyseed cofounder joins us to delve into the topic. We discuss key AI-driven processes you need to put in place, agentic AI, and ways teams can utilize AI to iterate and test marketing strategies faster. MORE Podcast Title On the Record by Leadpages
Podcast Description Welcome to "On the Record," the podcast that blends the best of business and music. Join us as we dive into timely, topical happenings in the business world. Our guests offer thought-provoking opinions and insights to help you scale your ideas, and our hard-hitting subject matter doesn't shy away from taking an unpopular stance. We’re disruptors and we don't apologize for it. Along the way, we'll sprinkle in discussions about our personal music interests, relating them back to the topic at hand and exploring the marketing lessons hidden inside the music.MORE Hosts Michael Sacca, Ryan Truax
Guest Rob Walling
Producer/Network Leadpages
Email ****@leadpages.com
Apple Rating 4.8/5Facebook 86.2KTwitter 27.3KInstagram 36.4K Avg Length 30 min Format Medium form Get Email Contact Get access to full database of 2.7M podcastsCreate podcast lists, export in spreadsheet or CSV file with email contacts and start your podcast outreach in minutes.Sign Up for Free with Email Continue with Google

2. How to Leverage AI to 5x Your Impact

Follow Play Jun 30, 2025 27:14
Website Apple
About Episode Rob Walling, Tinyseed cofounder joins us to delve into the topic. We discuss key AI-driven processes you need to put in place, agentic AI, and ways teams can utilize AI to iterate and test marketing strategies faster. MORE Podcast Title On the Record by Leadpages
Podcast Description Welcome to "On the Record," the podcast that blends the best of business and music. Join us as we dive into timely, topical happenings in the business world. Our guests offer thought-provoking opinions and insights to help you scale your ideas, and our hard-hitting subject matter doesn't shy away from taking an unpopular stance. We’re disruptors and we don't apologize for it. Along the way, we'll sprinkle in discussions about our personal music interests, relating them back to the topic at hand and exploring the marketing lessons hidden inside the music.MORE Guest Rob Walling
Producer/Network Leadpages
Apple Rating 5.0/5 Avg Length 35 min Format Medium form Get Email Contact

3. The SaaS Guide to Building with Purpose and Exiting with Pride with Rob..

Follow Play Jun 26, 2025 1:01:00
Website Apple Spotify
About Episode What if scaling your SaaS didn’t require burning out or selling your soul to venture capital? In this episode, Greg sits down with seasoned SaaS founder, author, and startup mentor Rob Walling for a candid conversation about what it really takes to build a sustainable, sellable SaaS business. Rob kicks things off by sharing how he stumbled into SaaS before it was cool, and how that journey led him to co-create TinySeed, an alternative funding model that puts founders first. He breaks down how TinySeed’s 12-month program works, who it’s for, and how it compares to traditional VC. But this episode isn’t just about funding, it’s about founder freedom. We dive deep into the psychological shifts that come with selling your business, how to recognize the right time to exit, and how to protect your energy both before and after a sale. Rob also shares the biggest traps SaaS founders fall into when chasing “growth at all costs” and the core traits he sees in founders who succeed. Whether you're bootstrapping, raising capital, or planning an exit, this episode is packed with honest, actionable insights that will help you scale smarter, and sell without regret. Topics Discussed in this episode: Rob’s background and how he got into SaaS (02:08) The origins of TinySeed and how it differs from Venture Capital (12:09) The opportunities that are created through selling your business (19:43) A breakdown of Tiny Seed’s 12-month program (22:19) The pros and cons of a “growth at all costs” mindset (28:32) The requirements needed to join Tiny Seed (30:20) The psychological effects of exiting your business (33:56) How to tell when to sell your business (39:40) How to avoid burnout before and after your exit (46:43) The characteristics that successful founders share (52:21) Mentions:  Empire Flippers Podcasts Empire Flippers Marketplace Create an Empire Flippers account Subscribe to our weekly newsletter Startups For The Rest Of Us podcast  Exit Strategy: The Entrepreneur's Guide to Selling Your Business without Regret TinySeed Sit back, grab a coffee, and learn how to take the next step in your SaaS journey with confidence.   MORE Podcast Title Empire Flippers Podcast
Podcast Description Fast. Safe. Simple. Investing in online business has never been easier. The Empire Flippers Podcast discusses buying and selling websites, investing in online assets and businesses, and discusses the successes and failures that come with online entrepreneurship.MORE Hosts Justin Cooke, Joe Magnotti
Guest Rob Walling
Producer/Network Justin Cooke and Joe Magnotti
Email ****@empireflippers.com
Apple Rating 4.9/5Facebook 29.7KTwitter 9.1KInstagram 4.6K Avg Length 49 min Format Long form Get Email Contact

4. #811 The Brutal Truth About Business Exits with Rob Walling

Follow Play Jun 12, 2025 49:46
Website Apple Spotify
About Episode Thinking of selling your business one day? Or never planning to? Either way, this conversation could change how you build. Rob Walling has seen it all. He’s exited his own SaaS company and helped thousands of founders grow and sell through TinySeed, MicroConf, and his podcast “Startups for the Rest of Us.” In this episode, he sits down with Dan to talk about what founders get wrong about selling, why most exits are emotionally brutal, and how to actually create a business that gives you freedom: whether or not you ever sell it. CHAPTERS (00:00:00) Why Exits Matter (Even If You Never Sell) (00:03:48) The Emotional Reality of Selling Your Business (00:08:35) What Your Business is Actually Worth (Valuation Benchmarks) (00:11:45) The $10M Dream: Who Gets There, Who Doesn’t (00:18:59) The SaaS Plateau: How to Know When You're Stuck (00:27:20) The 5 Marketing Channels Still Working in 2025 (00:30:23) Can Non-Technical Founders Still Win? (00:40:33) Two Traps Founders Fall Into When Selling a Business (00:46:50) Rob’s Book: “Exit Strategy” LINKS Rob’s book “Exit Strategy” (https://exitstrategybook.com/) Share your story/sponsor the pod (https://forms.gle/gKZFuwReHSvg8LD48) 22 free resources for founders (https://tropicalmba.com/resources) Connect with 1,000+ generous global entrepreneurs (https://dynamitecircle.com/) Read Dan’s book “Before the Exit” (https://www.amazon.com/Before-Exit-Thought-Experiments-Entrepreneurs-ebook/dp/B07BN2KD1J) Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. CONNECT WITH DAN Email Dan@tropicalmba.com Follow on X (https://x.com/TropicalMBA) Follow on Instagram (https://www.instagram.com/tropicalmba/) MORE EPISODES Our Lifestyle Business Non-Negotiables (https://tropicalmba.com/episodes/lifestyle-business-non-negotiables) ‘I’m Fiscally Bitcoin and Socially Ethereum’ (https://tropicalmba.com/episodes/greg-gerber-crypto-2020) Is Dropshipping Still a Valid Business Model? (https://tropicalmba.com/episodes/dropshipping-valid-business-model) The Consultant’s Handbook - How to Make Location Independent Income Quickly (https://tropicalmba.com/episodes/consulting) The Amazon Gold Rush (https://tropicalmba.com/episodes/amazongold) “Lifestyle Business” vs “Real Business” (https://tropicalmba.com/episodes/lifestyle-vs-real-business)MORE Podcast Title Tropical MBA: Entrepreneurship & Founder Lifestyle
Podcast Description With 10M+ downloads and thousands of listener meetups worldwide, the TMBA Podcast is the hub for 7 & 8-figure founders who’ve built life-changing businesses while attaining personal freedom. New episodes every Thursday morning.MORE Hosts Dan Andrews, Ian Schoen
Guest Rob Walling
Producer/Network Dan Andrews; Ian Schoen
Email ****@tropicalmba.com
Apple Rating 4.9/5Facebook 3.8K Avg Length 41 min Format Long form Get Email Contact

5. #136 Embracing Bootstrapping, VC Funding Myths, and Achieving Financial..

Follow Play Mar 24, 2025 35:46
Website Apple Spotify
About Episode Hey Listener! In the latest episode of Way of Product, I had the pleasure of chatting with Rob Walling, a serial SaaS entrepreneur, author, and SaaS investor at Tinyseed. Rob spends most of his time teaching people how to build million-dollar startups without venture capital. He also helps SaaS founders build incredible businesses. Rob has started six companies, written five books, Invested in 200+ startups, and has 15M+ podcast downloads on his podcast, Startups for the Rest of Us.Rob challenges the conventional narrative that startups must raise funding, instead advocating for bootstrapping as a viable path to success. He shares his 'one-nine ninety' rule, arguing that only a small percentage of startups should pursue venture capital. Rob draws on his journey as a successful tech entrepreneur who bootstrapped multiple companies, including Drip, which he sold in 2016.Connect with Rob on Linkedin. Listen now on Apple and Spotify. Actionable Takeaways ✅ Challenging the startup venture funding narrative. ✅ Profit over growth—choose freedom. ✅ Building resilience through hard decisions and luck.Time Stamps02:57 Real Estate vs. Software: Finding the Right Path 05:39 The Value of Bootstrapping 10:37 The Role of Developers in Startups 17:29 The Success of Drip 19:25 Making Hard Decisions with Incomplete Information 19:36 Launching and Finding Product-Market Fit 19:58 The Importance of Timing and Luck 22:39 Building an Audience and Brand 24:00 The Role of Hard Work, Luck, and Skill 27:28 Challenges in Product Management 33:22 The Value of Ownership and Decision Making 35:12 Final Thoughts and How to Connect Challenging the Startup Funding Narrative "There's this b******t narrative that everybody who does a startup has to raise funding. It's just not true." —Rob Walling Rob argues that it’s a myth that startups must always raise funding. His "one nine 90" rule suggests that only 1% of startups should consider raising venture capital while the majority could bootstrap successfully. Takeaway: Evaluate if external funding aligns with your startup goals or if bootstrapping might give you more freedom and control. Profit Over Growth—Choose Freedom "I haven't done anything for the money. I've done it all for the freedom." —Rob Walling Rob shared personal experiences, highlighting his journey from real estate investing to SaaS entrepreneurship. He emphasized that his drive was not to amass wealth but to gain control over his projects and time. Real estate investing might be good for building assets and wealth, but it is terrible when you want freedom and choice in how you spend your time. Takeaway: Focus on building businesses that align with your values and lifestyle. SaaS is a great asset class if you value freedom and autonomy.  An interesting takeaway is that you only need $4M in liquid assets when you retire to live a comfortable life and not have to work again. The game isn't to amass as much money as possible; it's to figure out what enough is for you and develop that muscle of knowing when you could stop. Building Resilience through Hard Decisions and Luck "As a founder, your job is to make hard decisions with incomplete information." —Rob Walling Walling asserts that hard work, luck, and skill are vital to entrepreneurial success. Success isn't guaranteed. That's the trade-off of going into the entrepreneurial journey. Considering that there's luck involved allows you to start making decisions that put you in a position to be lucky. Jason Fried, co-founder of Basecamp, told Rob that luck and timing were essential to the company's success. Given the competitive market, Launching Basecamp now would be more difficult. Takeaway: Accept that uncertainty is part of the journey. Use it to build resilience and trust in your decision-making abilities. Strategy is just positioning and segmentation. If you can get positioning and segmentation right (the “skill” aspect of success), you might have a better chance of being lucky and winning in that market segment.  Conclusion Rob Walling’s journey offers a fresh perspective on entrepreneurship, emphasizing freedom, autonomy, and the importance of resilience over long time horizons. Listen to the full episode to get all the context and stories behind these actionable takeaways. Thanks for reading The Way of Product! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.comMORE Podcast Title The Way of Product with Caden Damiano
Podcast Description The Way of Product is your graduate school focused on developing a taste for what “great products” look like. Conversations are two professionals talking shop about positioning, segmentation, excellent product design, and most importantly, taste. www.wayofproduct.comMORE Host Caden Damiano
Guest Rob Walling
Producer/Network Caden Damiano
Email ****@gmail.com
Apple Rating 4.0/5Twitter 62Instagram 295 Avg Length 44 min Format Long form Since Nov 2018 Get Email Contact