Frank Growth

Episode #227: Robin Izsak-Tseng — Marketing one brand to three audiences at once Most B2B companies fight to win one customer segment. WellHub has to win three at the same time. For marketers and operators running multi-audience, marketplace, or multi-country growth. Robin Izsak-Tseng is VP of global B2B marketing at WellHub, a corporate wellness platform serving over 40,000 companies across 18 co...

Episode #226: Seth Lowery — The $10M rule that kills good ideas, not just bad ones How to decide which growth bets to fund when every idea on the table already looks good. For marketing and growth leaders drowning in too many opportunities and a team that's too small to chase them all. Seth Lowery is VP of Marketing at Octane, a fintech that has originated over $8 billion in consumer loans and run...

Episode #225: Blakely Neilson — Building a high-growth EdTech brand when buyers aren't on LinkedIn This episode is a tactical playbook for marketing to a buyer that ignores LinkedIn, retargeting, and white papers: the school district. For operators and founders selling into education, or any relationship-first market where you can't performance-market your way to pipeline. Blakely Neilson came fro...

Episode #224: Alex Roy — Bootstrapping an AI company for 12 years, no funding He founded an AI company in 2014—when AI was a punchline—bootstrapped it with zero outside capital, and landed Fortune 50 clients. For founders and growth operators figuring out how to build (and sell) AI products in a market that shifts every few weeks. Alex Roy is the founder of SalesBox AI, a single-founder, bootstrap...

Episode #223: Divya Ramaswamy — Running one growth function across travel and fintech How a lean team runs acquisition, retention, and cross-sell across a travel marketplace and a fintech suite on a single brand. For growth leaders who own multiple products serving one customer across very different trust thresholds. Divya Ramaswamy runs growth across travel and fintech at Super.com—acquisition, a...

Episode #222: Simon Heyrick — How CFOs become real growth partners What it actually takes to turn your CFO into a growth ally instead of a gatekeeper. For founders, CEOs, and CMOs trying to align finance with marketing and growth investments. Simon Heyrick is the CFO of Sun World International and was Jason's CFO and then CEO at Soothe. In this conversation, Simon walks through what changes the mo...

Episode #221: John O'Donnell — Selling AI Trust When Your Best Outcome Is Invisible How do you sell infrastructure that works best when nothing bad happens? For GTM leaders, founders, and sellers building pipeline in category-creating, mission-critical sales motions. John O'Donnell leads go-to-market at Alice, where he sells AI trust and safety to the top foundation model companies and the enterpr...

Episode #220: Jacob Batist — Launching the first new health insurance company in Canada in 70 years How a European challenger broke into a market controlled by three incumbents — without a CEO on the ground, without brand awareness, and without growth-at-all-costs spend. For founders and growth leaders entering markets dominated by entrenched incumbents, where trust is the real constraint and spee...

Episode #219: Wade Lowe — Why GTM in the AI era is a Rubik's Cube The business takes on the personality of the founder. If there are problems, look at thyself. For founders running $5M–$50M companies trying to crack go-to-market when the playbook keeps changing. Wade Lowe is a 3x co-founder with two exits, focused on bootstrapping, AI, and mindset. He's led revenue at two Inc 500 companies (ranked...

Episode #218: Pashmina De Shon — Why Friction Is The Moat In Craft Chocolate How a bootstrapped founder built a $3M+ craft chocolate marketplace by owning the operational pain everyone else outsources. For e-commerce operators, bootstrapped founders, and brands weighing the jump from DTC to physical retail. Pashmina De Shon is the founder of Bar and Cocoa, a curated marketplace for craft chocolate...

Episode #217: Jeff Bishop Hill — How Swiss Army knife operators scale marketplaces What breaks first when a marketplace expands into new markets. This episode is for founders and operators balancing growth, ops, compliance, and enterprise sales at the same time. Jeff Bishop Hill breaks down what it takes to scale marketplaces when one operator is covering multiple functions at once. Drawing on his...

Episode #216: Matt Putra — Cracking paid lead gen for a services business How to lower lead costs by teaching instead of pitching. For service founders stuck with expensive, inconsistent lead flow. Matt Putra of EightX explains how he finally cracked lead generation for his fractional CFO business after spending $150,000 over 18 months on cold email, outbound, hiring, and agency support that did n...

Episode #215: Jay Sapovits — Turning branded merch into a strategic growth tool How to stop wasting money on swag that gets ignored. For founders and operators buying merch without a plan for impact. Jay Sapovits of Ink’d Stores explains how branded merchandise becomes useful when it starts with audience, objective, and distribution instead of a last-minute product order. He shares lessons from a...

Episode #214: Leigh Rowan — Building a premium service business without ads How to grow a premium service business through trust, referrals, and client retention. For founders and operators building high-touch services and trying to scale without paid acquisition. Leigh Rowan, founder and CEO of Savanti Travel, joins Jason Shafton to break down how he built a luxury travel management company servi...

Episode #213: Doug Breaker — Buying a SaaS instead of building from zero How to acquire a profitable SaaS with minimal upfront capital. For operators considering ownership but hesitant to start from scratch. Doug Breaker, CEO of Shoeboxed and former CEO of MD Hearing Aid, explains why he chose to buy a 20-year-old SaaS company instead of building one. After running an eight-figure DTC business, he...

Episode #212: Dan Kessler — Building organic growth beyond paid acquisition How to build consumer app growth without defaulting to paid media. For founders and operators scaling consumer subscription apps and looking for durable growth levers. Dan Kessler joins Jason Shafton to break down how he thinks about consumer growth across partnerships, product loops, and app portfolio strategy. Drawing on...

Episode #211: Elia Wallen — Building a $2B travel platform by serving SMBs How a founder built a multi-billion dollar company in an overlooked market. For operators deciding whether to chase hype markets or serve ignored customers. Elia Wallen is the founder and CEO of Engine, a business travel platform that grew out of his earlier company Travelers Haven. What started as a corporate housing servi...

Episode #210: Seif Salama — Why most product marketing fails to drive revenue Product marketing only matters if it changes pipeline, adoption, or retention. This episode is for founders, PMMs, and operators trying to make product marketing actually impact growth. Seif Salama joins Jason Shafton to break down what product marketing really does when it works. Seif has led product marketing across co...

HTML Episode #209: Pat Ryan — Building loyalty systems that protect margins How to design data systems that actually drive business outcomes. For operators building analytics, loyalty, or AI initiatives under real constraints. Pat Ryan, with experience at Discover, Organizing for Action, and United Airlines, joins Jason to break down what “data systems designed for growth” actually means in practi...

Episode #208: Lindsay Crittendon — Build a repeatable revenue system without spam Outbound email is an impression now—not a response channel. For seed to Series C revenue leaders building a real funnel and motion. Lindsay Crittendon (CRO, Taylor Bird) breaks down how to build revenue strategy that persists—grounded in how customers actually use your product, not heroics. She explains why the first...

Episode #207: Kushagra Shrivastava - Engineering serendipity in community and events How to design events where the right people actually meet and follow through. For founders and operators building communities, networks, or community-led growth. Kushagra Shrivastava is a builder and community investor behind Zoogler, a 40,000+ ex-Google alumni network. He explains how he defines “serendipity” as...

Episode #206: Steve Dennis — How to Write Like a Human in the Age of AI AI can generate endless copy. The new bar is making someone feel something. This episode is for founders, marketers, and anyone who writes for a living and wants their work to connect. Steve Dennis is a writer and ghostwriter who has shaped voices the world knows—including Andy Puddicombe at Headspace. Jason and Steve go back...

Episode #205: Jordan DiPietro — How to Turn an Audience Into a Community That Compounds Growth Most companies stop at audience. This episode shows you how to build community that creates its own pipeline. For founders and operators who want retention, not just reach. Jordan DiPietro has built audience-to-community flywheels at The Motley Fool, The Hustle (inside HubSpot), and as CEO of Hampton. In...

Episode #204: John Kennelly — Founders who hate sales still have to sell If sales feels intrusive, this episode reframes it as problem-solving. Built for founders avoiding sales calls, decks, and outreach. John Kennelly, Founder of I Hate Sales, works with founders who have never had a sales job and actively avoid selling. In this episode, he explains why sales fear is usually a mindset problem, n...

Episode #203: Trevor Houghton — How to buy growth without risking cash How founders use acquisitions to grow without betting the company. For operators considering their first inorganic deal. Trevor Houghton is CEO of Pass Galleries and a former private equity and corporate development operator. He breaks down how founders can use acquisitions to increase enterprise value without overextending cap...