The 16 Best Starting A Business Podcasts (2026)

Guy Raz is one of the best interviewers in podcasting, and How I Built This is the proof. Each episode features a long-form conversation with the founder of a well-known company, tracing the full arc from scrappy beginnings to the business you recognize today. We are talking about the people behind Airbnb, Spanx, Patagonia, Instagram, and hundreds more. Raz has a talent for getting founders past the rehearsed origin story and into the messy, uncertain moments where things almost fell apart.

The show runs about 45 minutes to an hour, dropping new episodes on Mondays and Thursdays. With over 820 episodes and nearly 30,000 ratings (4.7 stars), it is one of the most popular business podcasts in the world. The format is straightforward — it is essentially a biography told through conversation — but Raz's warmth and genuine curiosity keep it from feeling formulaic.

What makes How I Built This stand out from the flood of entrepreneur interview shows is the emphasis on failure and doubt. Founders regularly talk about the moments they were broke, rejected by every investor, or convinced the whole thing was going to collapse. Those stretches of honest vulnerability are what separate this from a press tour. The production is polished (it started at NPR before moving to Wondery), and there is a recurring "How You Built That" segment featuring everyday inventors. Fair warning: the ad breaks can be frequent, which some listeners find annoying. But the content between them is consistently strong.

Reid Hoffman co-founded LinkedIn, was an early investor in Facebook and Airbnb, and has been a partner at Greylock for years. So when he sits down with a founder and says "tell me how you actually scaled this," the conversation goes somewhere different than it would with a typical podcast host. He's not asking from curiosity alone -- he's stress-testing ideas against his own experience building and funding companies that went from nothing to billions.

Masters of Scale has produced over 660 episodes across its run, and the show has evolved from Hoffman as the sole host to include Jeff Berman and Bob Safian, who bring their own editorial and business journalism backgrounds. The format leans toward narrative storytelling rather than straight Q&A. Episodes are built around a central thesis -- say, how Zoom handled 30x growth almost overnight, or how DraftKings navigated regulatory uncertainty -- and weave in the guest interview around that structure.

The guest list is genuinely impressive: Eric Yuan, Gary Vaynerchuk, Padma Lakshmi, and hundreds of other founders and executives. The show tends to focus on the scaling phase rather than the initial startup grind, which makes it particularly useful for people thinking about growth-stage challenges. How do you maintain culture at 500 employees? When do you expand internationally? What does product-market fit actually feel like at scale?

The venture capital lens comes through naturally because Hoffman keeps circling back to how investors evaluate these inflection points. The production quality is polished -- almost too polished for some listeners who prefer a rawer format. But at a 4.6 rating from nearly 4,000 reviews, it clearly resonates.

Sam Parr sold The Hustle to HubSpot for a reported eight figures and Shaan Puri ran a product team at Twitch before its sale to Amazon. Now they sit across from each other and brainstorm business ideas out loud, and that freewheeling energy is exactly what makes My First Million so compelling for anyone thinking about starting something. The show publishes daily and has crossed 800 episodes since launching in 2019, consistently ranking among the top entrepreneurship podcasts in the country. The core format is refreshingly simple. Parr and Puri spot trends in the market -- a growing niche, an underserved customer segment, a business model working quietly in one industry that nobody has applied elsewhere -- and then riff on how they'd build a company around it. They've brainstormed everything from AI-powered tutoring platforms to niche newsletter empires to franchise models in overlooked service categories. Sometimes they bring on guests who've already built the kind of businesses they're dreaming up, which grounds the speculation in actual revenue numbers and operational realities. What keeps listeners coming back is the chemistry between the two hosts. Parr is the sales-minded operator who thinks in terms of customer acquisition and unit economics. Puri leans more toward product thinking and market psychology. They disagree regularly and aren't afraid to call each other's ideas bad, which makes the conversations feel honest rather than performative. Recent episodes have featured founders building tourism businesses in Jamaica, AI productivity tools, and direct-to-consumer brands scaling past their first million in revenue.

Pat Flynn got laid off from his architecture job in 2008 and decided to turn his LEED exam study guide into an online business. That one pivot became the foundation for everything Smart Passive Income has grown into over the past 17 years. The podcast has crossed 900 episodes, publishes twice a week, and Flynn has built it into a media brand that covers online courses, affiliate marketing, email list building, SEO, content creation, and team management -- basically the full toolkit for building an internet-based business from scratch. What makes Flynn distinctive in the crowded online business space is his transparency. He published monthly income reports for years, breaking down exactly how much money each of his revenue streams generated and where the numbers fell short. That level of openness attracted a community of people who were tired of gurus promising overnight riches without showing their work. Flynn's journey is also genuinely relatable for first-time entrepreneurs. He started with zero audience, built traffic through helpful content, and scaled gradually through affiliate partnerships and digital products rather than venture capital or outside funding. Recent episodes have covered 2026 marketing trends, content repurposing strategies, and how to build authority in a niche without a massive following. Flynn interviews both well-known creators and lesser-known entrepreneurs who've built quiet six-figure businesses in unexpected corners of the internet. The production quality is strong, episodes run about 30 minutes, and Flynn's teaching style is patient and clear without being patronizing. For someone just starting to think about building an online business, the back catalog alone is worth months of study.

John Lee Dumas was an Army officer and corporate employee who felt stuck before launching Entrepreneurs on Fire in 2012 with a premise most people thought was insane: a daily podcast interviewing entrepreneurs. That daily cadence has produced over 3,000 episodes and more than 100 million total listens, and the show still publishes every single day. Dumas has built EOFire into a media business generating seven figures of net revenue for eight consecutive years, and he's not shy about sharing those numbers publicly. The format is straightforward. Each episode runs 20 to 30 minutes and features Dumas interviewing a founder or business owner about their worst entrepreneurial moment, their biggest aha breakthrough, and the tactical advice they'd give someone just getting started. The consistency of the format is actually its strength -- after thousands of episodes, you start to see the patterns. The same mistakes come up again and again. The same turning points recur across wildly different industries. For someone at the very beginning of their entrepreneurial journey, absorbing those patterns is genuinely valuable. Dumas wrote a book called The Common Path to Uncommon Success that distills those patterns into a 17-step roadmap, and many episodes tie back to that framework. Recent episodes have covered tax planning strategies for new businesses, personal branding tactics, and time management for solo entrepreneurs. The show doesn't pretend to be investigative journalism or deep storytelling -- it's a daily shot of practical advice from someone who's actually in the arena, talking to others doing the same thing.

Nicaila Matthews Okome launched Side Hustle Pro in 2016 as the first podcast to specifically spotlight Black women entrepreneurs who scaled side projects into full-fledged businesses. Ten years and over 500 episodes later, the show has earned a 4.7-star rating from nearly 1,800 reviews and publishes new episodes weekly with no signs of slowing down. The premise is practical and specific. Okome interviews women who started businesses while holding down day jobs, then figured out when and how to make the leap to full-time entrepreneurship. Guests have included Myleik Teele, founder of curlBOX, Morgan DeBaun of Blavity, and Tiffany 'The Budgetnista' Aliche. Each conversation digs into the actual mechanics of getting started: how they funded their first product run, where they found their initial customers, what they wish they'd done differently in year one, and how they managed the transition from employee to founder. The show's strength is its specificity. Rather than broad motivational advice, Okome asks pointed questions about revenue, pricing, marketing channels, and the emotional reality of building something from nothing. A recent episode covered her own 12-week reset across health, money, and business operations, which shows the kind of behind-the-scenes honesty that separates this podcast from aspirational content that glosses over the hard parts. Side Hustle Pro is particularly valuable for anyone who wants to start a business but can't afford to quit their job first. The guests have all navigated that exact tension, and their stories provide a realistic roadmap for building something on the side before going all in.

The Pitch puts you in the room where startup founders ask real investors for real money. Host Josh Muccio has been running this show since 2015 as part of the Vox Media Podcast Network, and the format is unlike anything else in the podcast space. Each episode features a founder presenting their business to a panel of venture capitalists and angel investors, and you hear everything -- the pitch, the tough questions, the negotiations, the moments of doubt, and whether the investors actually write a check. Over 200 episodes have featured companies at various stages, from pre-revenue startups with nothing but an idea and a prototype to businesses already generating millions in annual recurring revenue. Recent pitches have included AI companies, consumer products, and marketplace startups, giving listeners a window into what investors are actually funding right now. What makes the show genuinely educational for aspiring entrepreneurs is hearing what investors push back on. The questions they ask reveal what matters: market size, unit economics, competitive moats, customer acquisition costs, and founder-market fit. You learn more about what makes a fundable business from listening to ten episodes of The Pitch than from reading most startup textbooks. The show also lets listeners invest alongside the panelists through its platform, which adds a layer of stakes that keeps everything honest. If you're building something and even thinking about raising money someday, this podcast gives you an unfiltered look at what that process actually involves.

Jason Calacanis has been doing This Week in Startups since 2009, making it one of the longest-running shows in the startup podcast space. Calacanis is a serial entrepreneur and angel investor -- he was an early backer of Uber, Calm, and Robinhood, among others -- and he brings a founder-first perspective that's more scrappy than polished. The show runs daily, blending news analysis episodes with founder interviews and live pitch sessions where entrepreneurs present their startups for real-time feedback.

The pitch episodes are where TWIST really shines. Founders get a few minutes to make their case, and Calacanis doesn't hold back. He'll tell someone their market is too small, their pricing is wrong, or that they should pivot entirely. It's direct in a way that most podcast hosts won't be, and listeners consistently point to these segments as the most valuable part of the show. Occasionally, Calacanis will actually invest on air, which adds genuine stakes to the format.

With 1,400-plus episodes, the archive is enormous. Recent content has shifted heavily toward AI agents and their impact on startups, reflecting Calacanis's own investments in the space. The show's energy is high and unapologetic -- Calacanis has strong opinions and shares them freely, which some listeners love and others find grating. He also promotes his own ventures more frequently than you might expect.

But here's the thing: if you're actually building a startup or thinking about angel investing, TWIST provides a practical, street-level view of the startup ecosystem that more institutional VC podcasts simply don't offer. The 4.2 rating from over 1,200 reviews reflects a loyal audience that keeps coming back.

Dan Andrews and Ian Schoen started Tropical MBA in 2009 while running a small manufacturing business from Southeast Asia, and what began as a blog about location-independent entrepreneurship has grown into a podcast with over 10 million downloads and 840 episodes. The show drops every Thursday and targets a specific audience that most business podcasts ignore: founders running seven- and eight-figure businesses who've already figured out the basics and are now wrestling with harder questions about growth, operations, lifestyle design, and whether the business they built is actually making them happy. The hosts bring the credibility of having done it themselves. They built and scaled multiple businesses, including a podcast production company and a conference series that brings together location-independent entrepreneurs from around the world. That conference community feeds directly into the podcast, which often features candid conversations with founders in their network about problems they're actually facing -- not theoretical case studies from business school. Recent episodes have tackled questions like whether your business can outperform the S&P 500, how to structure equity splits with a co-founder, and what happens when you hit a growth ceiling and have to decide between staying lean or adding headcount. The tone is pragmatic and grounded, with none of the hustle-culture hype that dominates much of the entrepreneurship podcast space. Andrews and Schoen talk openly about their own mistakes and the tradeoffs they've made along the way. For founders who are past the idea stage and deep in the messy middle of actually running a company, Tropical MBA speaks their language.

Henry Lopez built this podcast around a straightforward promise: teaching people the practical mechanics of starting, running, and growing a small business. Since 2016, he's published over 600 weekly episodes and earned a 4.7-star rating from 500 reviews, which speaks to how consistently the show delivers on that promise. Lopez himself is a serial entrepreneur and small business owner, not a journalist or consultant observing from the outside, and that operational experience shapes every conversation. The format alternates between two types of episodes. Solo shows tackle specific business topics -- writing a business plan, choosing a legal structure, understanding cash flow, hiring your first employee, picking the right insurance -- the kind of nuts-and-bolts questions that every first-time business owner has but that most podcasts skip over in favor of flashier content. Interview episodes feature small business owners sharing their real experiences, from franchise operators to service providers to product companies. The guests aren't typically Silicon Valley unicorn founders. They're people running restaurants, consulting firms, cleaning companies, landscaping businesses, and e-commerce stores. That makes the advice directly transferable for the vast majority of people who want to start something that doesn't involve venture capital or tech. A recent episode featured Shannon Bailey discussing marketing in the AI era for small businesses, which is exactly the kind of timely, practical guidance the show does well. Lopez asks clear, focused questions and keeps episodes in the 30 to 40 minute range. The massive back catalog functions like a self-paced small business curriculum that you can dip into based on whatever challenge you're facing this week.

Kimberly Brock has 26 years of entrepreneurial experience and she's turned that into a top 1% globally ranked podcast specifically for women who are starting or pivoting their businesses. She's Just Getting Started has grown to over 330 weekly episodes since its launch, earning a 4.9-star average from over 300 reviews, and Brock publishes consistently with a recent episode dropping in February 2026 on the three things you absolutely need to know before launching a business. The show sits at a specific intersection that's underserved in the podcast landscape: practical business coaching with faith-based encouragement, aimed at women who are taking their first real steps into entrepreneurship. Brock doesn't assume her listeners already have MBAs or startup experience. She covers fundamentals like choosing a business model, setting prices that actually generate profit, managing the fear that comes with putting yourself out there, and building systems that don't require working 80 hours a week. The format mixes solo teaching episodes where Brock walks through specific frameworks and strategies with interview episodes featuring women entrepreneurs at various stages of their journeys. What makes the show work is Brock's directness. She doesn't sugarcoat the difficulty of starting a business, but she also doesn't drown listeners in complexity. Her coaching background shows in how she breaks big decisions into manageable steps and addresses the mindset barriers that stop people from taking action. For women who feel overwhelmed by the idea of starting a business and want guidance from someone who genuinely understands that starting point, this podcast meets them exactly where they are.

Courtland Allen built Indie Hackers into one of the most influential communities for bootstrapped founders on the internet before Stripe acquired it, and the podcast was where many of the community's best conversations happened in long-form audio. Over 290 episodes, Allen and his brother Channing interviewed founders who built profitable online businesses without venture capital -- people running SaaS tools, newsletters, marketplaces, and digital products that generated real revenue with small teams or as solo operators. The show's back catalog is a gold mine for anyone considering bootstrapping a business. Guests shared specific revenue numbers, customer acquisition strategies, pricing experiments, and the daily realities of running a company without outside funding. Episodes featured founders at every stage, from someone making a few hundred dollars a month from a side project to operators running multi-million dollar businesses with tiny teams. The conversations were technical and specific in a way that most entrepreneurship podcasts avoid -- you'd hear about conversion rate optimization, choosing between different tech stacks, content marketing funnels that actually worked, and how to find your first ten paying customers. Allen's interviewing style was curious and detail-oriented, always pushing past surface-level answers to get at the mechanics of what actually drove growth. The podcast's last new episode was in June 2023, making it a concluded show, but the archive remains one of the best resources available for anyone who wants to build a profitable business on their own terms without chasing unicorn valuations.

Alex Lieberman co-founded Morning Brew as a side project while he was still in college, grew it into a daily newsletter reaching millions of subscribers, and then sold it to Business Insider for a reported $75 million. Founder's Journal is where he unpacked the lessons from that journey and applied them to the broader challenges of building a business from the ground up. Over 630 episodes, Lieberman shared the kind of insider perspective that most business media can't offer because he was actively living through the startup experience while recording. The show's format was refreshingly direct. Episodes typically ran 10 to 20 minutes and focused on a single topic -- how to negotiate equity, why most content strategies fail, the psychology behind pricing decisions, how to hire your first employee without making expensive mistakes, and what to do when your co-founder relationship starts breaking down. Lieberman drew heavily from his own experiences at Morning Brew, but also brought in frameworks from other founders and operators he'd connected with through the company's network. What made the show particularly valuable for aspiring entrepreneurs was Lieberman's willingness to talk about the emotional and psychological dimensions of founding a company, not just the tactical ones. He covered imposter syndrome, decision fatigue, the loneliness of being a CEO, and the tension between ambition and burnout. The podcast produced its last episode in June 2025, but the archive remains packed with practical wisdom from someone who built a media company worth tens of millions before turning 30.

Pat Walls built StarterStory.com into one of the largest databases of founder case studies on the internet, with thousands of interviews documenting how real people started real businesses. The podcast is the audio extension of that mission, and it brings the same focus on specifics that made the website valuable. Each episode features Walls sitting down with a founder who shares the actual numbers -- how much they invested to get started, what their monthly revenue looks like, where their customers come from, and the specific decisions that moved the needle. With 36 episodes published since its launch and new episodes dropping twice a week as of February 2026, the show is still relatively young but already delivering the kind of detailed founder interviews that the Starter Story brand is known for. Recent guests have included a founder who grew a browser plugin to $12,000 a month, bootstrapped SaaS operators, agency builders, and e-commerce entrepreneurs. The businesses featured tend to be attainable rather than aspirational -- these aren't billion-dollar unicorn stories but rather profitable companies built by people who figured out how to serve a specific market well. Walls asks the questions that aspiring entrepreneurs actually want answered: how much did it cost to start, how long until it was profitable, what would you do differently, and what does a typical week look like. The podcast pairs well with the Starter Story website, where each featured business gets a full written case study with detailed financials. For anyone in the early stages of thinking about what kind of business to build, this show delivers concrete blueprints from founders who are actually doing it.

Ola Williams brings over 20 years of experience as a retail entrepreneur, fintech founder, and certified financial coach to The Small Business Startup School, and that combination of street-level business experience and financial expertise gives the show a practical edge that most entrepreneurship podcasts lack. With 46 episodes published weekly, the show explores business strategies through a lens that combines financial literacy with retail psychology -- teaching new business owners not just how to sell but how to understand the money side of their operations from day one. The interview format brings in experts across different domains relevant to starting and growing a business. A recent episode featured veteran salesman Glenn Poulos discussing the emotional dynamics of closing deals, drawing from his book 'Never Sit in the Lobby.' Other episodes have covered topics like managing cash flow as a new business, understanding your customer's buying psychology, building a financial foundation before you scale, and the tax considerations that trip up first-time entrepreneurs. Williams earned a perfect 5-star rating, and the show maintains a focused scope that works in its favor. Rather than trying to cover every aspect of entrepreneurship, it zeroes in on the intersection of business operations and financial decision-making. For someone starting a retail business, a service company, or any venture where understanding money management is make-or-break from the very beginning, the show provides the kind of grounded financial education that most founder-focused podcasts skip entirely. Each episode runs about 30 to 40 minutes, long enough to get into substance but short enough to fit into a lunch break.

Robin Waite is a UK-based business coach and author who built The Fearless Business Podcast around a core argument: most new business owners fail not because their product is bad but because their mindset around pricing and selling is broken. Over 175 episodes, Waite has developed a focused framework built on three pillars -- creating a sustainable offer you genuinely enjoy delivering, understanding pricing psychology so you can charge two to three times what you currently do, and building lead generation systems that convert consistently. The show earned a perfect 5-star rating, and Waite's coaching background comes through in how he structures each episode. Rather than just interviewing guests and hoping useful advice emerges naturally, he pulls conversations back to actionable frameworks that listeners can implement in their businesses that week. Topics range from the psychology of premium pricing to why most service businesses undercharge by 50 percent or more, and from building productized service offerings to understanding why some marketing generates leads and some just generates noise. Waite's own journey informs the advice. He ran a web design agency, burned out, reinvented himself as a business coach, and wrote 'Take Your Shot' -- a book about pricing strategy disguised as a golf fable. That experience of building, struggling, and rebuilding gives him credibility when he tells listeners that the biggest barrier to business success is usually sitting between their ears. The show's most recent episodes aired in early 2025, so the release schedule has slowed, but the existing catalog remains a concentrated course in business mindset and pricing strategy for anyone just getting started.