10 Best Andrew Ackerman Podcasts in 2025
Explore the Best Podcasts Featuring Andrew Ackerman
Here are 10 Best Podcasts Featuring Andrew Ackerman worth listening to in 2025.
Follow All1. DWAVC: Andrew Ackerman | Ep. 36
Follow Play Apr 15, 2025 1:48:41
Website Apple Spotify
About Episode What do tiddlywinks, a quarter trick, and a failed Palantir deal have in common? They all show up in Andrew Ackerman’s one-of-a-kind path from founder to family office director, accelerator operator, and venture capitalist to now SPV syndicate lead and author. Andrew pulls no punches on what most startups get wrong — from pitch decks that waste space to market slides that make investors roll their eyes. He shares lessons learned from backing 70+ startups on how to actually stand out in a noisy fundraising environment, why EdTech broke his heart, and how day drinking helped him write The Entrepreneur’s Odyssey — a startup guide founders might actually finish. Also in this episode: - His “accidental” real estate empire - EdTech’s big COVID moment (and what came after) - The one thing every founder should know about market sizing - And yes, Andrew answers the Fidelity Five Questions. If you’ve ever wondered what VCs really think when they see your deck — this one’s for you! Episode links: www.AndrewBAckerman.com Entrepreneur's Odyssey Episode timestamps: 00:00 DWAVC Episode: Andrew Ackerman 03:28 Guest Introduction and Background 05:25 March Madness Predictions 07:42 Andrew's Origin Story 16:18 Parenting in the Digital Age 30:27 Andrew's Unique Skills 31:01 Discussing the New Book 31:52 Inspiration Behind the Book 32:15 Writing Process and Challenges 37:23 Character Development 40:37 Market Sizing and Go-to-Market Strategies 44:14 Importance of Value Proposition 01:13:52 Fundraising Insights 01:15:27 Navigating VC Funding Strategies 01:17:19 Challenges for Non-Ivy League Founders 01:20:09 Importance of Warm Intros 01:22:33 Accessing Capital Outside Major Hubs 01:24:37 The Role of Location in Startup Success 01:27:09 Influence of Science Fiction on Entrepreneurship 01:29:56 The Rise of PropTech 01:41:28 Fidelity Five Questions MORE Podcast Title DrinksWithAVC (DWAVC)
Podcast Description Grab a drink and join Vik (Green Cow Venture Capital) and Bree (Cooley) as they sit down with top venture capitalists to uncover the stories behind the spreadsheets. Each episode blends laughter, quirks, and candid conversation with practical frameworks founders can use to build, grow, and fundraise more successfully. If you’re a startup founder, VC, or LP, this show helps you get to know the people you may be partnering with for the next 7–10 years. From Tuvan throat singing and mini piano playing to our signature “Fidelity Five” lightning round, you’ll discover surprising sides of the investors shaping the startup ecosystem. We feature leaders from powerhouse firms like Bessemer, Costanoa, Scale VP, and Lightspeed, as well as emerging funds such as Touring, Better Tomorrow Ventures, Hustle Fund, and Precursor. Expect founder-tested advice, real talk about venture, and plenty of laughs along the way. New episodes drop monthly. Pour your favorite drink and dive in.MORE Hosts Bree Hanson, Vikram Lakhwara
Guest Andrew Ackerman
Producer/Network Bree Hanson & Vikram Lakhwara
Email ****@burklandassociates.com
Apple Rating 5.0/5Twitter 62 Avg Length 93 min Format Extended Get Email Contact 
2. The Entrepreneur’s Odyssey: Teaching Startup Success Through Story
Follow Play Sep 14, 2025 36:15
Website Apple Spotify
About Episode In this episode, host Brooke-Sidney Harbour sits down with angel investor and startup mentor Andrew Ackerman to unpack his new book, The Entrepreneur’s Odyssey: A Novel Approach to Startup Success—a business book told as fiction. Andrew shares why story beats slides for learning, how the hero’s journey mirrors the founder journey, and the practical “why now” lens he uses to evaluate ideas (including AI). If you’re launching your first idea or scaling your next milestone, this conversation gives you mindset, models, and memorable stories to strengthen every “link” in your startup chain. Listen/Watch • ? Podcast: Available wherever you listen to podcasts • ? Full YouTube Episode: https://youtu.be/73L26bI5sbQ • ? Book: The Entrepreneur’s Odyssey — https://amzn.to/489s4KW “Your startup is a chain, not a rope. One weak link can break the whole thing.” — Andrew Ackerman Connect with Andrew: Website: https://andrewbackerman.com Instagram: https://www.instagram.com/andrewbackerman/ LinkedIn: https://www.linkedin.com/in/andrewbackerman/ X/Twitter: https://x.com/andrewackerman ⸻ Key Takeaways • Story sticks. Founders remember lessons best when they’re anchored in real startup stories—not bullet lists. • The Odyssey lens. Like Odysseus, great founders are resourceful “hackers” who go over, under, around, or through obstacles. • Two must-haves for a “novel” biz book: engaging narrative and accurate, actionable advice. • Use narrative in your pitch. Choose the right story arc—origin story (personal mission) or “big problem just became solvable” (dramatic hook). • Team slide ≠ resumes. It’s “why we win at this—now,” not just who you are. • Experimentation mindset. Build quick, cheap tests to validate what actually matters; don’t hide where “the light is better.” • “Why now” matters. AI (and other inflections) can be the catalyst—but only if it truly changes what’s possible. • Bar goes up as costs go down. Tools make building easier; investors expect more traction earlier. • Success, redefined. Beyond returns, learning and playing with new tools (incl. AI video and code) can be part of the win. ⸻ Practical Frameworks & Examples • The Chain Test: Identify each critical link (problem, timing/“why now,” solution, GTM, unit economics, team unfair advantage, moat). Shore up the weakest one first. • $100 Test: Before raising, spend ~$100 on ads to validate CPC/CTR and sanity-check your growth model. • Founder Narrative Options: 1. Missionary Origin (personal stake) • 2) Inciting Incident (the problem just became solvable) • Pricing Story Example: Subway ride → flat fare vs. per-unit pricing → opens to “all-you-can-eat,” usage-based, or share-of-savings models. ⸻ Rapid-Fire with Andrew • Morning ritual: Coffee ☕ • Must-read for founders: Mastering the VC Game by Jeff Bussgang: https://amzn.to/4pnkEdq • One word for his philosophy: Experimentation • Focus song: “Son of a Preacher Man” ⸻ Time Stamps 0:00 Welcome & intro 1:18 Why tell startup lessons through fiction 3:40 Story as the most memorable teacher 4:10 “Odyssey” and the hacker-hero founder 5:48 Balancing narrative with actionable tactics 7:30 Writing challenges & classroom edit (goodbye F-bombs) 10:50 Giving each character a distinct voice 12:05 Using storytelling in pitches that land 15:01 What Andrew looks for on the team slide (“why we win”) 17:01 Urgency vs. strategic focus—design cheap tests 21:02 AI as today’s “why now” (and when not to use it) 26:00 Lower build costs, higher traction bar 28:23 The “startup chain” metaphor 30:50 Success, learning, and playing with AI tools 32:23 From cube to founder—who should go for it 33:49 Rapid-fire round 35:34 Closing & how to connect ⸻ Mentioned in the Episode • Book: The Entrepreneur’s Odyssey by Andrew Ackerman: https://amzn.to/489s4KW • Book (ops classic): The Goal by Eliyahu Goldratt: https://amzn.to/46d11vM • Book (VC perspective): Mastering the VC Game by Jeff Bussgang: https://amzn.to/4pnkEdq • Tooling themes: AWS, APIs, GitHub, AI coding assistants, gen-AI video ⸻ Work With Brooke-Sidney / The Soul Story® Agency Want help crafting the story that investors, customers, and the press remember? • ✍️ Author & Founder Story Architecture™ (done-with-you / done-for-you) • ? Media & Messaging for launches and fundraising • ? Book coaching / ghostwriting for founder brand & authority ? Book a strategy session: https://bit.ly/BJHbookchats ⸻ Support the Show • Subscribe on YouTube: [Subscribe + ?]: https://youtube.com/@soulstoryshow • Follow on Instagram: https://instagram.com/soulstoryshow • Share this episode with a founder who needs a “why now” boost. ⸻ #SoulStoryShow #Entrepreneurship #Startups #AngelInvesting #Storytelling #AI #FounderLife #PitchDeck #BookTalk #bookcoach #authorcoach #booktube #booktuber #writerscommunity #authortube #authortubers #bookreview #ghostwriter #writer #author #booklover #booklovers MORE Podcast Title Soul Story® Show with Brooke-Sidney
Podcast Description A show that celebrates the power of books and storytelling to transform lives. Through author interviews, book chats, and cultural conversations, we explore the stories that shape us—and inspire you to write and share your own.MORE Guest Andrew Ackerman
Apple Rating 5.0/5 Avg Length 38 min Format Medium form Get Email Contact
3. 27 - From Founder to Investor: Lessons on Startup Survival and the ‘Three..
Follow Play Oct 09, 2025 46:16
Website Apple Spotify
About Episode Andrew Ackerman has seen startups from every angle, as a founder and investor. In this episode of Innovator Insights, Andrew joins Henrik Johansson to share the frameworks, stories, and lessons that shape successful founders, and the painful truths behind those who fail. You’ll hear: ? Why startups are like chains, not ropes, and how one weak link can break everything ? The “three dimensions of pain” every product must solve to be fundable ? Why storytelling sticks better than advice when mentoring founders ? How to validate assumptions with nothing but a spreadsheet and $100 in Facebook ads ? The journey behind his new book The Entrepreneur’s Odyssey, and how he turned years of startup lessons into a story that teaches better than a manual ever could A must-listen for entrepreneurs, investors, and anyone looking to understand what really makes or breaks a startup. ? Listen on Spotify, Apple, Pandora, YouTube, Audible, and iHeartRadio. MORE Podcast Title Innovator Insights
Podcast Description This podcast celebrates the visionaries, the risk-takers, and the disruptors who are shaping the future of consumer product innovation and e-commerce. We love to spotlight consumer product entrepreneurs, e-commerce titans, and sustainability champions to share their insights and expertise. Think you'd be a great guest on our show? Apply at https://podcast.gembah.com/podcast-guest-home-page.MORE Guest Andrew Ackerman
Producer/Network Innovator Insights
Apple Rating 5.0/5 Avg Length 41 min Format Long form Get Email Contact
4. 43. The Entrepreneurial Odyssey of Andrew Ackerman
Follow Play Sep 03, 2025 35:13
Website Apple Spotify
About Episode Join us as we dive into the entrepreneurial journey of Andrew Ackerman, a two-time exit founder and author of "The Entrepreneurial Odyssey." Discover how Andrew navigated the startup world, from his early days inspired by family entrepreneurs to his ventures in tech and investment. Gain insights into the challenges and triumphs of building successful startups and the lessons learned along the way. Key Takeaways: Andrew's unique path from consulting to entrepreneurship The evolution of tech startups and their impact Strategies for resilience and success in the startup ecosystem The importance of passion and understanding your role as a founder Andrew Ackerman - Entrepreneur, Investor, and Author Connect with Andrew: LinkedIn: Andrew Ackerman Book: "The Entrepreneurial Odyssey" #Entrepreneurship #Startups #AndrewAckerman #TechInnovation Don't miss out on future episodes! Subscribe now to stay updated on the latest insights from industry leaders. MORE Podcast Title Start to Scale: The Founder's Podcast by Gildre
Podcast Description Most founder podcasts are fluff. Not this one. Real founders. Real strategies. Real results. Hosted by Taiga Gamell, he interviews founders who’ve scaled companies, raised capital, and know what actually works. Every episode: 30-50 minutes with one founder who’s been from start to scale. The pivots that saved them. The mistakes that cost six figures. The growth hacks that 10x’d revenue. No theory. No BS. Just tactical advice from entrepreneurs who’ve raised millions, built teams, and created real exits. Subscribe. Take notes. Build something that matters.MORE Guest Andrew Ackerman
Producer/Network Gildre.com
Avg Length 42 min Format Long form Get Email Contact
5. Construir, Invertir y Escalar Startups: La Visión de Andrew Ackerman
Follow Play May 26, 2025 43:59
Website Apple Spotify
About Episode En este episodio platicamos con Andrew Ackerman, inversionista, exdirector de Urban Tech en Dreamit Ventures y autor de The Entrepreneur’s Odyssey, un nuevo libro que funciona como guía práctica para quienes buscan lanzar y escalar una startup. Conversamos sobre los errores más comunes que cometen los fundadores, cómo validar ideas desde el día uno, y cómo levantar capital con una narrativa clara y un producto validado. Andrew comparte insights clave desde su experiencia trabajando con cientos de startups en sectores como proptech, fintech y el futuro del trabajo. Una conversación llena de consejos para quienes están en el camino emprendedor. MORE Podcast Title Creating Results
Podcast Description Bienvenido a Creating Results, el pódcast para conocer más sobre los líderes del sector inmobiliario y emprendedores en general que están transformando el mundo con nuevas tecnologías, conceptos y propuestas innovadoras. El propósito del pódcast es que juntos aprendamos más acerca de nuevas experiencias y tendencias, modelos disruptivos, transformación digital, nuevas soluciones del real estate; así como temas de actualidad como la aplicación de inteligencia artificial, blockchain, sustentabilidad, entre otros. MORE Host Carlos Rousseau
Guest Andrew Ackerman
Producer/Network Carlos Rousseau
Email ****@collective-re.com
Avg Length 37 min Format Medium form Get Email Contact
6. Lessons From 70 Startups: What Makes a Hands-On Business Win
Follow Play Oct 31, 2025 49:46
Website Apple
About Episode What if the lessons that power tech startups could also help your blue-collar business grow? In this episode of The Aro Benaiah Show, host Aro Benaiah sits down with Andrew Ackerman a two-time startup founder and mentor who’s helped over 70 entrepreneurs launch and scale successful ventures. Andrew opens up about growing up in a family built on hustle, transitioning from consulting into full-time entrepreneurship, and how he now mentors small business owners including tradespeople on growth, testing ideas, and leadership. He shares practical takeaways: why saying “yes” before you’re fully ready can fuel momentum, how to validate ideas fast, and why empathy and grit are key for long-term success. If you’re a hands-on business owner or trade entrepreneur ready to level up your mindset and operations, this conversation will give you both clarity and courage. ? Watch now and learn real startup lessons you can apply to your trade or service business today. Learn more about Andrew here: https://www.andrewbackerman.com/ #AndrewAkama #TheAroBenaiahShow #StartupMindset #TradeEntrepreneur #BlueCollarSuccess #SmallBusinessGrowth #EntrepreneurMindset #LeadershipLessons #StartupMentor #HandsOnBusiness MORE Podcast Title Aro Benaiah Show
Podcast Description Welcome to Aro Benaiah Show, where we dive into the journeys of successful blue-collar entrepreneurs. Join us as we interview industry leaders from various trades to uncover their inspiring stories. We'll explore how they got started, what motivated them, the challenges they faced, and how they overcame obstacles to achieve success. Whether you're considering a career in a blue-collar field or looking to pivot into entrepreneurship, these real-life blueprints will guide you on your path to success. Tune in and get inspired to build your future!"MORE Guest Andrew Ackerman
Apple Rating 5.0/5 Avg Length 34 min Format Medium form Get Email Contact
7. Inside Real Estate Tech Investing: Wins, Lessons & Opportunities, with..
Follow Play Jul 02, 2025 44:29
Website Apple Spotify YouTube
About Episode Andrew Ackerman is the Head of REACH Labs at Second Century Ventures, the strategic venture arm of the National Association of Realtors® (NAR). Backed by NAR, SCV invests in early-stage PropTech and construction tech companies, providing them with access to a vast network of real estate professionals and industry expertise. A former entrepreneur, angel investor, and accelerator director at Dreamit Ventures, Andrew has backed 70+ startups and designed structured programs to help founders raise capital and close deals faster. He is also the author of “The Entrepreneur’s Odyssey,” a story-driven startup guide, and a frequent contributor to Forbes, Propmodo, and other leading publications. (01:19) – Andrew Ackerman's Journey in PropTech (03:06) – Evolution of the PropTech Landscape (06:40) – The Role of Reach Labs, Second Century Ventures and NAR (10:06) – Challenges in Real Estate Transactions (13:00) – Venture Returns in PropTech (21:01) – Feature: Blueprint - The Future of Real Estate - Register for 2025: The Premier Event for Industry Executives, Real Estate & Construction Tech Startups and VC's, at The Venetian, Las Vegas on Sep. 16th-18th, 2025. (23:03) – Qualifying Investment Opportunities (23:32) – Challenges in Portfolio Construction & Valuation Dilemmas (30:00) – The Role of Venture Debt (35:59) – The Entrepreneur's Odyssey (29:22) - Collaboration Superpower: Richard Nixon ? Learn more:➡️ Visit REACH Labs ➡️ Andrew Ackerman on LinkedIn ➡️ Read The Entrepreneur's Odyssey ? Feature: ➡️ Blueprint - The Future of Real Estate - Register for 2025: The Premier Event for Industry Executives, Real Estate & Construction Tech Startups and VC's, at The Venetian, Las Vegas on September 16th-18th, 2025. ? Connect with Tangent: ➡️ Edward Cohen on LinkedIn ➡️ Jeff Berman on LinkedIn ➡️ Zach Aarons on LinkedIn ➡️ Tangent on LinkedIn Disclaimer: Tangent podcast is for entertainment and informational purposes only, you should not construe any such information or other material as legal, tax, investment, financial, or other advise. Nothing contained on our program constitutes a solicitation, recommendation, endorsement, or offer by Tangent, Camber Creek, MetaProp, or any third party guest to buy or sell any securities, public or private, other financial instruments or funds. MORE Podcast Title Tangent ? Proptech
Podcast Description A podcast community for Proptech and Real Estate leaders, investors, operators and innovators. A new era is upon us. Tangent💚Proptech unites Proptech founders💡, Real Estate investors and operators🏢, Venture Capital investors, urban leaders🏙 and passionate creators🌎 who are improving our communities and cities. Join us to learn how we can solve present day challenges with innovative technology and greater collaboration. Join VC investors Jeffrey Berman and Zach Aarons, and Proptech entrepreneur Edward Cohen, to learn about housing innovation, the future of work and climate tech. We examine these themes through interviews and conversations with Proptech CEO's, real estate owners and operators, and venture investors, and how we can leverage tech and collaboration to help solve the housing crisis, figure out the future of work and how to decarbonize the built environment. If you would like to get your company’s or organization’s mission featured on Tangent, email us at community@tangentproptech.com. Stay curious and always be learning! 🤓MORE Hosts Edward Cohen, Jeffrey Berman, Zach Aarons
Guest Andrew Ackerman
Producer/Network Edward Cohen, Jeff Berman & Zach Aarons
Email ****@gmail.com
Apple Rating 4.9/5Twitter 179 Avg Length 37 min Format Medium form Get Email Contact
8. S6E2: Demystifying Startups, Angel Investing & Career Pivots with Andrew..
Follow Play Oct 22, 2025 36:04
Website Apple Spotify
About Episode In this episode, we sit down with Andrew Ackerman, a serial entrepreneur turned early-stage investor who’s backed over 70 startups and led innovation efforts across industries. Andrew is currently Strategic Advisor and Head of REACH Labs at Second Century Ventures, and has held roles ranging from Managing Director at Dreamit Ventures—where he launched edtech and urbantech accelerators—to COO of a summer camp platform and Head of Product at Kaplan. He shares how he’s navigated a dynamic career, made smart pivots, and leveraged each opportunity to grow his impact across entrepreneurship, education, and investment. We dive into his work with Dreamit Access and Dreamit Athena supporting underrepresented founders, demystify the angel investing landscape, and explore the practical wisdom behind his newly published book The Entrepreneur’s Odyssey—a startup manual wrapped in a novel. Andrew also reflects on the lessons he’s learned about capital raising, technical and financial skills, and using writing as a tool to drive change in the innovation ecosystem. If you’re curious about building, investing, or simply making bold career moves, this episode is packed with insights you won’t want to miss. MORE Podcast Title The Impact Agenda
Podcast Description In the 21st century, there’s no limit to what social good can look like. Join Princeton students Evey Howe and Elise Kratzer as they talk to trailblazers, creators, leaders and team players to redefine and expand the boundaries of a “social impact” careers beyond the traditional definitions and dispel the myths that you can’t create a successful or profitable career that focuses on and incorporates social impact. Follow us as we initiate, integrate, and inspire service in our lives and others, together!MORE Guest Andrew Ackerman
Producer/Network Evelyn Howe and Elise Kratzer
Apple Rating 5.0/5 Avg Length 35 min Format Medium form Get Email Contact