The 15 Best Entrepreneurship Podcasts (2026)

Guy Raz interviews the founders behind the world's most recognizable companies, and the conversations consistently go deeper than the usual startup success story. How I Built This releases episodes on Mondays and Thursdays, running anywhere from 45 minutes to an hour and a half. Each interview follows a founder from their earliest days — the moment of inspiration, the initial failures, the funding struggles — through to the company becoming a household name. Raz has interviewed the people behind Airbnb, Spanx, Patagonia, Instagram, and hundreds more across 818 episodes. The show holds a 4.7-star rating from nearly 30,000 reviews. Raz is an exceptionally skilled interviewer. He asks follow-up questions that other hosts would miss, and he creates space for founders to talk about doubt and failure, not just triumph. The "Advice Line" episodes add a nice variation where previous guests mentor new entrepreneurs with specific problems. The educational value comes not from abstract business theory but from pattern recognition — listen to enough of these stories and you start noticing what successful founders have in common, and more interestingly, where they diverge completely. It is a masterclass in entrepreneurship delivered through personal narrative, and one of the best business podcasts for anyone who learns through stories rather than textbooks.

Sam Parr and Shaan Puri have turned brainstorming sessions into appointment listening. Each episode of My First Million is essentially two friends with serious business credentials riffing on startup ideas, breaking down trends, and occasionally bringing on guests to stress-test their thinking. Sam sold The Hustle newsletter to HubSpot, Shaan led Bebo through its acquisition by Twitch for $25 million, and together they bring a rare combination of operational experience and creative instinct.

The format is loose in the best way. Some episodes are rapid-fire idea sessions where Sam and Shaan generate ten business concepts in thirty minutes. Others are deep-dives into a single trend or industry they think is about to explode. The chemistry between the hosts is genuine -- they challenge each other, build on half-formed ideas in real time, and aren't afraid to call something stupid when it is. That honesty makes the show feel like eavesdropping on a private conversation between two people who actually know what they're talking about.

With nearly 800 episodes by early 2026, the show has built a massive library of ideas, frameworks, and case studies. Recent episodes have covered AI business opportunities, goal-setting frameworks, and business ideas predicted to take off in 2026. The production is clean but unfussy -- the focus stays on the ideas rather than slick editing.

The show works best for people who think entrepreneurially about the world, the kind of person who walks into a laundromat and immediately starts calculating unit economics. Sam and Shaan model a way of seeing opportunity everywhere, and that perspective is infectious even when you never act on a single idea they pitch.

Tim Ferriss approaches interviewing like a scientist running experiments. He sits down with world-class performers, from NFL Hall of Famers like Steve Young to Grammy-winning musicians like Tim McGraw, and methodically picks apart their routines, habits, and decision-making processes. The result is a podcast that consistently delivers actionable takeaways you can actually use.

With 857 episodes and a 4.6-star rating from nearly 16,000 reviews, The Tim Ferriss Show has been one of the most popular podcasts in the world for over a decade. Ferriss became famous for The 4-Hour Workweek, and that same obsession with efficiency and optimization runs through every interview. Episodes typically run 90 minutes to two and a half hours, though he occasionally drops shorter guided meditation sessions too.

The guest range is impressive. You will hear from neuroscience researchers, survival show champions, performance coaches, and bioelectricity pioneers all within a few weeks of each other. Ferriss prepares obsessively for each conversation, and it shows. He asks specific, detailed follow-up questions that reveal things guests have never discussed elsewhere. The tone is more buttoned-up than Rogan, less comedy and more intellectual rigor, but the long-form interview format and genuine curiosity about how exceptional people operate makes this a natural next stop for JRE listeners who lean toward the self-improvement side.

Four billionaire friends arguing about technology, politics, and markets for two hours at a time -- that's All-In in a nutshell, and it turns out to be wildly compelling. Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg each bring different perspectives rooted in their own investment portfolios and operating experience. Chamath runs Social Capital, Jason is an angel investor and media figure, Sacks built Yammer and now runs Craft Ventures, and Friedberg founded The Production Board after working at Google.

The show launched during the COVID lockdowns in 2020 and quickly became one of the most influential business podcasts in the world. The four hosts self-describe as "besties," and the dynamic between them ranges from genuine intellectual debate to good-natured roasting. They disagree frequently and vocally, which is the show's greatest strength. You're not getting a single worldview here; you're getting four distinct frameworks applied to the same events.

Recent episodes have tackled AI developments, de-dollarization, political predictions for 2026, and the California governor's race. The show's influence has grown to the point where the hosts conducted an interview with President Trump in the Oval Office, and their annual All-In Summit in 2025 drew thousands of attendees to Los Angeles for a weekend that included a takeover of Universal Studios.

The entrepreneurship angle is baked into everything they discuss. Even when the topic is geopolitics or regulation, the analysis comes through the lens of how it affects startups, venture capital, and market opportunity. If you want to understand how Silicon Valley's most connected investors actually think about the world in real time, there's no better source.

Ben Gilbert and David Rosenthal have turned business history into appointment listening. What started in 2015 as a podcast about tech acquisitions has evolved into something much more ambitious: multi-hour episodes they call "conversational audiobooks" that dissect how the world's most important companies were actually built. Each episode of Acquired now reaches over a million listeners, making it the number-one technology podcast on both Apple Podcasts and Spotify.

The research that goes into each episode is staggering. When Ben and David covered TSMC, they flew to Taiwan to conduct a rare English-language interview with founder Morris Chang. Their episodes on companies like Coca-Cola, IKEA, Hermes, and Nintendo often run three to four hours and contain the kind of detail you'd normally find only in a dedicated business biography. They celebrated their tenth anniversary in January 2026 with a special episode featuring Michael Lewis.

The format works because Ben and David genuinely enjoy the material. Their excitement is palpable when they uncover a strategic decision that shaped an entire industry, and they do an excellent job of explaining why a particular move mattered in its historical context. The show has also expanded into live events, including a Radio City Music Hall show featuring Jamie Dimon and Andrew Ross Sorkin that was released as the podcast's first "concert film."

Acquired is essential listening for anyone who wants to understand not just what successful companies do, but why they made the specific choices that set them apart. The episodes are long, but they earn every minute. If you care about business strategy at a deep level, you'll find yourself reorganizing your schedule to make time for each new release.

Reid Hoffman has spent decades building and investing in companies that changed how we live and work, and on Masters of Scale he brings that hard-won perspective to long-form conversations with founders and CEOs who've actually done the thing. Each classic episode is built around one of Hoffman's counterintuitive scaling theories — like the idea that you should do things that don't scale first, or that the best companies let fires burn. Guests include everyone from the founder of Zoom to Gary Vaynerchuk, and the show layers in additional commentary and cameo voices that give each story real texture. Beyond the flagship format, the Rapid Response episodes tackle breaking business situations in near-real time, pulling in leaders who are navigating crises or pivots as they happen. Co-hosted by Jeff Berman and Bob Safian alongside Hoffman, the show puts out new episodes twice a week and has built up over 660 episodes and nearly 4,000 ratings on Apple Podcasts (sitting at 4.6 stars). The production quality is genuinely polished — think narrative storytelling meets business interview — and it works because Hoffman asks the kinds of follow-up questions that only someone who's been in the room can ask. If you're building something or leading a team through growth, this one earns its spot in your rotation.

John Lee Dumas has published a new episode of Entrepreneurs on Fire every single day since 2012. That's not a typo -- the show drops seven days a week and has accumulated over 4,500 episodes and 175 million total listens. The sheer volume is both the show's defining feature and its competitive advantage. No other entrepreneurship podcast comes close to that output.

Each episode follows a tight format: JLD interviews a successful entrepreneur, digs into their journey, extracts their key lessons, and keeps the whole thing under 30 minutes. The brevity is intentional. JLD knows his audience -- busy founders and aspiring entrepreneurs who want concentrated insight they can absorb during a commute or workout. The consistency of the format means you always know what you're getting, which has built an intensely loyal listener base.

JLD's own story adds credibility. After leaving the Army, he struggled to find his path before launching EOFire. He's been transparent about his revenue (the show has generated seven figures in net annual income for eight consecutive years) and publishes monthly income reports. His book, The Common Path to Uncommon Success, codifies his 17-step framework for building a business. In January 2026, he served as master of ceremonies at the Podcast Hall of Fame Induction Ceremony at Podfest Expo.

The daily format means some episodes hit harder than others, which is inevitable at this volume. But the archive is enormous and searchable, and the best episodes contain genuinely actionable advice from founders who have built real businesses. For someone early in their entrepreneurial journey who wants daily motivation paired with tactical insights, EOFire delivers more consistently than any other show in the space.

Jason Calacanis has been covering the startup world since 2009, making This Week in Startups one of the longest-running shows in its category. Jason is an angel investor with early bets in Uber, Robinhood, and Calm on his resume, and he brings that deal-flow perspective to every episode. The show covers startups, technology, markets, media, and whatever else Jason finds interesting that week, which turns out to be a lot.

The format splits between solo commentary episodes where Jason breaks down the week's biggest startup and tech stories, and interview episodes where he sits down with founders, investors, and operators. Jason's interview style is direct and sometimes confrontational -- he'll push back on founders who dodge questions or pitch vague ideas. That bluntness can be polarizing, but it consistently produces more honest conversations than the typical softball podcast interview.

Recent 2026 episodes have covered the intersection of SpaceX and xAI, AI agent security risks, and practical advice for early-stage founders on saving cash and prioritizing distribution. Jason and his co-host Alex bring a mix of macro-level analysis and ground-level founder advice that keeps the show relevant for both investors and operators.

The show publishes multiple episodes per week, which means it functions almost like a news source for the startup ecosystem. If something big happens in tech on Tuesday, Jason is talking about it by Thursday. That timeliness, combined with Jason's extensive network and willingness to say things other podcast hosts won't, makes TWiST a staple for anyone who wants to stay current on what's actually happening in the startup world rather than reading about it a week later.

Hala Taha built Young and Profiting from a side project into one of the top-ranked business podcasts in the world, and then used that momentum to launch YAP Media Network, a podcast network representing major shows hosted by Jenna Kutcher, Amy Porterfield, Tori Dunlap, and John Lee Dumas. YAP Media was on pace to hit eight figures in revenue in 2025, which makes Hala herself one of the most successful entrepreneurs in the podcasting space.

The show is structured as "mini-masterclasses" where Hala interviews business icons and thought leaders. The guest roster is stacked: GaryVee, Alex Hormozi, Mel Robbins, Reid Hoffman, Tom Bilyeu, and Codie Sanchez have all appeared. Hala's interviewing style is focused and efficient -- she clearly prepares extensively and steers conversations toward specific, implementable takeaways rather than letting guests run through their standard talking points.

What makes the show distinctive is its cross-disciplinary approach. Episodes cover entrepreneurship, sales, marketing, psychology, and personal development, and Hala connects ideas across those domains in ways that feel natural rather than forced. A conversation about neuroscience might lead directly into a marketing strategy discussion, and both halves feel relevant.

The production is polished, episodes are well-edited, and Hala has a talent for making complex business concepts accessible without oversimplifying them. She also practices what she preaches -- building YAP Media into a major network while hosting the podcast gives her a level of credibility that purely theoretical hosts lack. If you want actionable business and personal development content from someone who is actively building a company in real time, Hala's show consistently delivers.

Harry Stebbings started The Twenty Minute VC in 2015 with fifty dollars and zero contacts in venture capital. His first guest was Guy Kawasaki. A decade later, the show has become one of the most important podcasts in the venture capital ecosystem, with past guests including Sequoia's Doug Leone, Benchmark's Bill Gurley, Spotify's Daniel Ek, LinkedIn's Reid Hoffman, and Snowflake's Frank Slootman.

The original concept was simple: keep interviews to twenty minutes and focus exclusively on venture capital. The show has since expanded beyond that time constraint, but the efficiency remains. Harry packs more substance into his episodes than most hosts manage in twice the runtime. He publishes multiple episodes per week, splitting between VC investor interviews and founder conversations, with each format bringing a different angle on the startup ecosystem.

Harry's trajectory is itself an entrepreneurial story worth studying. The podcast's success gave him the deal flow and relationships to launch 20VC, his own venture capital fund. That dual role as both media figure and active investor means he has a level of access that pure podcast hosts can't match. When Harry interviews a GP at a top fund, he's speaking as a peer, not an outsider, and that dynamic produces more candid conversations.

The show is essential for anyone who wants to understand how venture capital actually works -- not the mythologized version, but the real mechanics of fundraising, deal evaluation, portfolio management, and founder-investor dynamics. Recent episodes have covered major market developments including AI investment trends and tech industry consolidation. For founders seeking venture funding, listening to 20VC is essentially free education on how your potential investors think.

Josh Muccio created something that shouldn't work as well as it does: a podcast version of Shark Tank that's actually better than the TV show for learning about entrepreneurship. The Pitch records real founders making real pitches to real investors, with real money on the line. There's no scripting, no dramatic music cues, and no post-production editing to manufacture tension. The tension is already there because the stakes are genuine.

The show has had an interesting journey. It started in 2015 and was eventually acquired by Gimlet Media, then went to Spotify when Gimlet was acquired. After Gimlet was sold, Josh bought The Pitch back in 2022, took it independent, and partnered with Vox Media for distribution. Season 15 was streaming on Spotify in early 2026, with 207 episodes in the catalog. Josh himself is a founder-turned-podcaster-turned-VC, having started his first company in college, which gives him a unique understanding of both sides of the pitch table.

What makes the show valuable for listeners is hearing how investors actually evaluate ideas in real time. You hear the questions they ask, the concerns they raise, and the reasoning behind their yes-or-no decisions. It's an education in how startup funding works that no textbook can replicate. Some pitches succeed, some fail, and the most instructive episodes are often the ones where investors pass and explain exactly why.

The format is tight -- episodes run around 20 to 30 minutes -- and the variety of businesses that come through keeps things from getting repetitive. If you've ever wondered what it actually sounds like when a founder asks an investor for money, this is the show.

Courtland Allen and his brother Channing Allen built Indie Hackers into the go-to community for entrepreneurs who want to build profitable businesses without raising venture capital. The podcast is the audio arm of that community, featuring interviews with founders who have turned side projects and small ideas into sustainable income streams, often while working solo or with tiny teams.

The show occupies a specific and important niche in the entrepreneurship podcast world. While most business podcasts celebrate massive funding rounds and billion-dollar exits, Indie Hackers focuses on the founder who built a $30K/month SaaS product, or the developer who turned a weekend project into a six-figure business. These stories are arguably more relevant and replicable for the average listener than yet another unicorn founder interview.

Courtland's own journey mirrors the community he built. He's a former Y Combinator founder and MIT alum who created indiehackers.com, which was acquired by Stripe. In a full-circle moment, Indie Hackers has since spun out from Stripe, and the Allen brothers are now indie hackers themselves, building the company from $0 as an independent operation.

The conversations tend to be detailed and technical. Courtland asks about revenue numbers, growth strategies, tech stacks, and the specific decisions that moved the needle. There's a transparency in these interviews that you rarely find elsewhere -- guests share their actual numbers because the Indie Hackers community has established that as the norm. For developers, designers, and creators who want to build something profitable on their own terms, this podcast provides both the tactical playbook and the proof that it's possible.

Nick Loper has spent over twelve years as the founder of Side Hustle Nation, and his podcast is the engine that drives the whole operation. With approximately 700 episodes and over 100,000 listeners, The Side Hustle Show has become one of the most comprehensive resources for people who want to earn money outside their day job without quitting it.

The show's scope is deliberately broad. Nick covers online businesses, freelancing, gig economy opportunities, investing strategies, and offline service businesses with equal enthusiasm. A recent episode featured a guest who built a pet waste removal company to 350 recurring customers in three months. Another explored franchises as a lower-risk alternative to starting from scratch. That variety means the show surfaces ideas you'd never encounter on a typical tech-focused entrepreneurship podcast.

Nick's interviewing style is practical and grounded. He's not interested in hype or get-rich-quick promises. Each episode is structured to give you a clear understanding of what a particular side hustle involves, how much it costs to start, what the realistic income potential looks like, and what the actual day-to-day work entails. He asks the questions a skeptical friend would ask, which saves you from having to figure out the gotchas yourself.

The podcast is part of the YAP Media Network, which speaks to its quality and reach. For someone who wants to explore income diversification without the pressure of going all-in on a startup, Nick provides a steady stream of tested ideas. He's earned the informal title of "the king of side hustles," and the depth of his back catalog justifies it. Each episode is a self-contained playbook you can evaluate and potentially act on within a week.

Arvid Kahl doesn't just talk about building bootstrapped businesses -- he does it in public while recording the podcast. Arvid is the founder of Podscan, a podcast monitoring platform, and he uses The Bootstrapped Founder as a vehicle to document his journey in real time. That build-in-public approach gives the show an authenticity that interview-only podcasts can't match. When Arvid talks about the challenges of growing a SaaS product, he's drawing from that morning's work, not memories from five years ago.

The show publishes twice weekly with two distinct formats. Wednesday episodes feature in-depth interviews and masterclasses with subject matter experts. Friday episodes are solo deep-dives where Arvid explores a specific topic relevant to the founder and creator journey. Recent episodes have covered building with Claude Code for six months, how programmatic SEO investments compound over time, and why "follow your passion" is consistently ranked as the most frustrating advice entrepreneurs receive.

Arvid's background adds substance to the show. He previously co-founded FeedbackPanda, an ed-tech SaaS that he and his partner bootstrapped and sold. That exit gave him both the credibility and the financial runway to focus on building and teaching in the bootstrapping space. His writing (he's the author of "The Embedded Entrepreneur" and "Zero to Sold") reinforces the podcast's analytical, framework-driven approach.

The show is tailor-made for software founders who want to build profitable businesses without outside funding. Arvid's audience tends to be technical, and the conversations reflect that -- discussions about tech stacks, automation, and product development sit alongside marketing strategy and audience building. It's one of the few podcasts where the host's own company serves as a live case study that listeners can follow week to week.

Andrew Warner has been interviewing founders on Mixergy since 2009, making it one of the oldest continuously running startup podcasts in existence. Andrew's own credentials are solid -- he built a $30-million-per-year internet business before pivoting to media -- and that experience shows in how he conducts interviews. He asks challenging, sometimes uncomfortable questions because he knows the polished version of a startup story is rarely the useful one.

The show's archive is massive, with hundreds of episodes spanning nearly two decades of the startup ecosystem. That longevity means the catalog captures entire eras of entrepreneurship: the early social media boom, the mobile revolution, the SaaS explosion, and now the AI wave. Recent episodes from early 2026 have featured entrepreneurs like Kasey Grelle, whose firm Aux Insights became the outsourced CMO for private equity companies.

Andrew's interviewing approach is distinctive. He prepares extensively and isn't satisfied with vague answers. When a founder says "we grew quickly," Andrew wants the specific numbers. When someone claims they pivoted successfully, he asks exactly what failed first and how much money they lost. That persistence produces conversations with more substance than the typical friendly founder chat.

Mixergy has always positioned itself as education rather than entertainment. Many episodes include explicit frameworks and step-by-step breakdowns that listeners can apply to their own businesses. Andrew also offers paid courses through the Mixergy platform, but the free podcast episodes stand on their own as valuable resources. For founders and aspiring entrepreneurs who want unvarnished startup stories with real tactical depth, Mixergy's seventeen-year library is one of the richest archives in podcasting.