How Strava Does B2B with Jonny Ross of Strava

In this episode of Cash Machines, Tom Hunt deconstructs the $20 million dollar bootstrap model behind the Acquired podcast. He examines how founders Ben Gilbert and David Rosenthal maintain 90 percent profit margins with a lean team of three. The breakdown explores their research process, where months of preparation and 40 sources culminate in three-hour deep dives into global brands. Tom also identifies their most sophisticated lever: Acquired Capital, a venture fund that invests back into show sponsors to create a self-reinforcing loop of content and capital. This is a masterclass for entrepreneurs building high-margin media assets that prioritize depth over volume.

In this episode of Cash Machines, Tom Hunt dissects the business of John Lee Dumas, Host of Entrepreneurs On Fire, to discuss the transition from capital gains to cash flow and the mechanics of a $22,000,000 profit empire. He shares a detailed analysis of how the business generated nearly $28,000,000 in lifetime revenue despite revenue and profit peaking as early as year two. Tom also examines the three strategic levers used to sustain a 96% margin: a lean operational team, zero-cost customer acquisition, and tax arbitrage in Puerto Rico. He reveals the philosophy driving the show’s rebrand, emphasising the historical importance of prioritising free cash flow over the common obsession with capital gains. Finally, he outlines the vital lesson that a business needn't maintain a growth trajectory to achieve an extraordinary lifestyle and financial outcome for its founder.

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt is joined by Nick Hague, host of the World's Greatest Business Thinkers podcast and Author of the book B2B Customer Experience. They discuss Nick’s 24-year journey of scaling B2B International from a bedroom startup into a global powerhouse with ten offices and £20m in revenue. Nick details the "marketing obsession" and relentless brand building required to maintain growth through multiple recessions, sharing tactical stories of the early-stage hustle used to secure major contracts with brands like Renault. The episode dives into the complexities of navigating a four-year earn-out within a global corporate structure following an acquisition by Dentsu and explores Nick’s evolution into a full-time podcaster and his transition into the padel sports market.

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt is joined by Dom Hawes, Builder CEO and Small & Mid-Cap M&A Specialist. They discuss the critical distinction between capacity and capability acquisitions, why deal structure creates more leverage than headline price, and frameworks for identifying achievement-driven founders. Drawing on lessons from over 13 agency deals and a formative early failure, Dom explores the "Club Rules" model for integration - centralising back-office functions whilst preserving the creative autonomy and brand identity that makes agencies valuable. He breaks down the art of strategic deal sequencing and building a reputation that secures inbound deal flow without entering competitive auctions. Dom also reveals his unconventional tactic for testing founder honesty under pressure to ensure long-term alignment and success.

In this episode of Confessions of a B2B Entrepreneur, Michael Bunting is joined by Tom Hunt, CEO at Fame. They discuss the paradox of "knowing nothing" while building a successful business, the discipline required to lead 70 remote staff through rituals, and the psychological drivers behind an obsession with growth. Tom shares his journey from 17 failed ventures to founding a leading podcast agency, offering a candid look at how "meddling" can disempower teams and why "action bias" is both a founder's greatest strength and a potential weakness. The conversation delves deep into the "Secret Life of Leaders", exploring how childhood patterns influence professional ambitions and the vital difference between chasing values and practising virtues like presence.

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt is joined by Sid Jashnani, Founder at Momentum. They discuss the "crash landing" of Sid's first retail venture and how managing a €200 million project for Nokia Siemens helped him identify a gap in the B2B tech market. Sid explains using EOS as a "defibrillator moment" to professionalise his agency and step back from daily operations. We explore his transition into building a 15-company HoldCo through vertical integration, where he launched 14 complementary brands to own the supply chain. Sid breaks down his 50/50 equity framework for hiring top-tier leaders and how he now balances coaching in his pursuit of Ikigai. This episode offers a definitive blueprint for scaling with discipline and moving from operator to investor.

In this greatest hits episode of Confessions of a B2B Entrepreneur, Tom Hunt is joined by Lara Acosta, Founder at LA Digital, to discuss the psychology behind building a massive LinkedIn presence, the transition from solopreneur to agency owner, and the framework for creating high-impact personal brands that drive business growth. Lara shares her journey of growing to over 110,000 followers (noting she has since surpassed 300,000) and explains why "fame" is a critical asset for modern B2B founders, exploring how authentic storytelling and consistent engagement can bypass traditional sales hurdles. She breaks down her approach to content pillars, the importance of "renting" an audience before owning one, and how to maintain a relentless posting schedule without burning out. This masterclass in digital authority reveals the power of putting a human face to a B2B business and provides a step-by-step guide to scaling a profile that converts.

In this episode of Confessions of a B2B Entrepreneur, host Tom Hunt is joined by Tim Cakir, Founder of AI Operator, to deliver a masterclass on achieving operational efficiency through AI. Tim shares his journey from a growth consultant to an "AI-first" specialist, detailing how the real secret to growth lies in optimising systems and removing repetitive, boring tasks. He reveals that the biggest easy wins for B2B automation involve reporting, streamlining data access, and answering internal FAQs, offering a case study where a custom GPT saved field sales teams fifteen hours a month each. Tim tackles the fear of job redundancy directly, arguing that learning AI makes an employee "unstoppable," enabling a team of 75 to generate the output of 750. Furthermore, he delves into the transformative "agentic era," explaining how new tool-calling agents - which can perform deep research and run virtual computers - are allowing entrepreneurs to "vibe code" and build bespoke internal tools faster than ever before.

In this episode of Confessions of a B2B Entrepreneur, host Sam Winsbury is joined by Tom Hunt, Founder and CEO of Fame, who details the counter-intuitive strategy behind scaling his remote B2B podcast agency to over £4M ARR. Tom reveals how he obsessively focuses on client retention as the foundation for growth, enabling him to run a low-cost operational model (zero office, minimal ads) to ensure "no-brainer" client pricing. He explains his shift to a CEO role focused on strategic acquisitions and high-leverage problems, detailing his unique remote leadership approach: promoting the entire management team internally from entry-level. Crucially, Tom shares the biggest mistake that slowed his growth: a painful lack of focus from attempts to build software and expand service lines outside his core offering.

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt speaks with Aditya Shivkumar, Co-founder of Resolve Disputes Online (RDO), about his transition from lawyer to global legal-tech founder. Aditya reveals how the analytical skills honed in litigation became the most valuable asset for their successful B2B pivot into Online Dispute Resolution (ODR). He shares the entrepreneurial mindset that allowed RDO to treat the COVID-19 crisis as a "watershed moment" for growth and securing funding. The conversation culminates with Aditya detailing how he applies Jose Mourinho's strategic 'Catenaccio' philosophy directly to winning high-value B2B contracts.