Funds and Founders: Untold Journeys Behind Their Breakthroughs

James Brewer went from being Import Yeti’s 3rd user to its co-founder—and helped scale it to 150K+ paying users and 2M monthly visitors. In this episode of Funds and Founders, he breaks down how import/export data can power sales, how to turn sweat equity into real ownership, and the systems that helped build a multi-million dollar bootstrapped SaaS. 💡 Whether you're in logistics, SaaS, or trying to break into tech—this episode is packed with actionable frameworks on: - Sales with data - Startup equity - Scaling without VC - Automation stacks that save 10+ hours/week - And the power of never taking “no” as the final answer 📬 Want to try Import Yeti’s premium tools? Watch the full episode @FundsAndFounders Timestamps: 00:00 – James Brewer on retention and the surprising start of Import Yeti 01:20 – From user #3 to co-founder: the cold email that changed everything 03:10 – The pitch mistake that taught James how to actually sell 05:00 – Using import/export data to close million-dollar clients 07:00 – What makes global logistics shockingly inefficient 09:00 – The sweat equity deal: how James negotiated his way in 11:15 – Building trust without funding: early growth, first users, and retention 13:30 – The automation stack that saves him 10+ hours/week 15:45 – Why James still handles support tickets personally 17:20 – Growth without VC: systems, obsession, and ownership 19:50 – Customer feedback vs. product focus: what they say “no” to 22:00 – How Import Yeti avoids getting outpaced by copycats 23:30 – The three biggest use cases driving 2M monthly visits 26:00 – Sales vs. product: how to balance short-term wins and long-term moat 28:10 – Lessons from scaling a “boring” SaaS in a niche market 30:00 – Founder conflicts, and why their partnership actually works 33:00 – Most SaaS founders get sales wrong — here’s what to fix 35:15 – How to earn founder-level equity even if you weren’t there day one 37:30 – Final advice: Build something useful. Stay in the game. Get obsessed. 39:30 – Where to find James + how to access Import Yeti’s premium features

Newsletters are not dead, Dylan from Growth in Reverse breaks down how indie founders and B2B operators are building 5-figure audiences and monetizing with just email. He shares the underrated metric every newsletter creator should track, how to launch a newsletter from scratch, and why owning your distribution is your biggest unfair advantage. We also go deep on - Sponsorships - Paid ads - Personal vs Company branding - How to stay consistent even when life gets in the way. Whether you're just starting or scaling, this episode is a must-listen. Timestamps: 00:00 - Quick intro & Dylan plugs 01:30 - The most overlooked truth about newsletters 02:55 - One North Star metric every founder should track 05:00 - Why owning your distribution is non-negotiable 06:45 - How to start a newsletter from zero 08:30 - Educate, Inform, Entertain: The content trifecta 09:40 - How to *sell* through newsletters without annoying your readers 11:55 - When to start thinking about sponsorships 13:45 - Monetizing early: ads, partnerships & paid growth 17:00 - Newsletter commitment: Why 10+ editions matter 20:05 - Favorite growth channels: Paid, organic, lead magnets 24:00 - Facebook ad hack that landed 20+ subscribers before launch 27:10 - Building your system: SOPs, templates & content blocks 30:00 - Should you steal playbooks? How to filter growth tactics 33:00 - Writing vs Talking: Choosing the right medium 36:00 - Guest posts, collaborations & ownership issues 38:05 - Smart ways to collect feedback from your audience 42:10 - Building brand: Personal vs Company vs Thematic 45:30 - When personal branding blocks startup acquisitions 47:00 - Behind the scenes at Growth in Reverse 50:00 - Final tips for founders building in public

In this episode of Funds and Founders, we sit down with Michael, co-founder of Q Branch and Populace, who shares how he's helping international startups enter the U.S. and launching a fintech platform to fight financial inequality. From federal contracts and government culture to empowering underserved Americans through passive investing and discount networks, Michael breaks down the hard truths of money, persistence, and building in Austin. What You’ll Learn: - Why Most Startups Fail to Enter the U.S. Market - The Broken Banking System and a Grassroots Fix - Real Talk on Financial Literacy - Startup Persistence & the 18-Month Grind - What U.S. Founders Can Learn From International Builders Timestamps: 00:00 - Intro & How They Met 00:30 - What Is Q Branch? 01:30 - Helping International Startups in the U.S. 02:10 - Government Contracts & Go-to-Market 03:20 - Populist: A Fintech for the 99% 05:00 - Breaking Down Financial Literacy 06:00 - How Populist Reverses the Bank Model 07:40 - Making Passive Investing Accessible 09:10 - Michael’s Entrepreneurship Origin Story 11:00 - Lessons From Federal Contracting 13:00 - How Q Branch Got Its First Deal 15:00 - Founder Persistence & Mentality 17:00 - Talking About Ideas Early 19:00 - U.S. vs International Founders 21:00 - Austin’s Startup Community 25:00 - Picking the Right Ecosystem 29:00 - Building Populace: From Idea to Launch 32:00 - Real Cost of Building a Fintech Startup 34:00 - Launch Strategy & What’s Next 35:00 - Final Advice for Founders

Cody Anderson is back for Part 2! In this episode, we dive deep into what actually works when it comes to go-to-market (GTM) strategies — especially for early-stage startups. Cody shares lessons from scaling Carta to $9B, building Tommy Homes, and advising multiple startups on GTM, brand building, and AI-led growth.We cover:- B2B vs B2C GTM approaches- Why most startup advice is noise- Personal brand vs company brand- Building AI agents for sales, marketing & ops- The future of one-person billion-dollar companies🔗 Guest: [Cody Anderson](https://www.linkedin.com/in/codyanderson)Timestamps:00:00 – Cody's journey: From Carta to Tommy01:48 – Why Cody’s GTM perspective is unique03:38 – GTM strategies: B2B vs B2C05:45 – The myth of "funnels" and what works now08:16 – Tools, outbound, and unit economics09:55 – Personal brand vs company brand12:02 – How narrow should your ICP targeting be?15:09 – B2C GTM: Channels, content & challenges17:54 – Finding what works for you as a founder20:16 – Shift to content is greater than followers (thanks TikTok)23:13 – Niching down and the rise of shareable content24:07 – Tommy Homes: Challenges in educating the market26:34 – Building trust in a complex real estate model28:49 – Services-as-Software: AI as the co-founder31:05 – The one-person Slack-powered startup34:00 – Why personal stories is effective than generic advice38:18 – What’s next for Tommy42:10 – Final advice: Ignore the noise, trust your path

What happens when a startup sales pro burns out and decides to start a podcast? In this episode of Funds and Founders, we sit down with Pat Killoren — host of Lone Startups who shares his wild journey from scaling beer brands and influencer platforms to building community-led content in Austin. 🎙 We go deep into: Building sales teams as a founder The mistakes startups make in GTM strategy Burnout, pivots, and personal reinvention How to monetize podcasts through real partnerships (not just ads) Whether you're a builder, creator, or investor, this episode will leave you with tangible lessons on growth, niche branding, and sustainable success. TIMESTAMPS: 00:00 – Intro: Who is Pat Callaghan? 01:00 – Why he chose Austin and non-tech founders 03:30 – His journey from beer to blockchain 06:00 – What is Go-To-Market ? 08:00 – The Enterprise Trap: Why startups jump too soon 10:00 – How scrappy founders should build sales 14:30 – Why you shouldn’t send proposals too early 16:00 – How founders waste time chasing the wrong customers 18:00 – Picking the right channels: The Web3 sales story 21:00 – Cold outreach vs sniper sales: What works today 23:00 – How to hire your first sales hire (without getting burned) 25:00 – Why he quit sales and started a podcast 28:00 – The admin pain of podcasting no one talks about 30:00 – The monetization struggle: why brands hesitate 32:00 – Seasons vs weekly: how he’s structuring Lone Startups 36:00 – Format talk: from nature podcasts to 3D LED sets 40:00 – Roundtable format: a future idea for deep-dive episodes 44:00 – The mental blocks of podcast production quality 46:00 – Tools + Tech Stack for running the show 52:00 – Why video editing has become his new obsession 54:00 – Question for the next guest 56:00 – Where to follow Pat & closing thoughts

In this episode of Funds and Founders, we sit down with the co-founder and CEO of FletchPMM—a company that’s helped over 350+ B2B startups fix their biggest problem: nailing positioning and messaging.We go deep into:The $1.5M journey in just 20 monthsWhat most B2B startups get wrong about value propsWhy building distribution first beats productThe real meaning of product-market fitHow to use LinkedIn to grow a 7-figure businessWhether you're bootstrapping or venture-backed, this is the episode every founder needs to hear.Timestamps:00:00 – Intro & Plug: What FletchPM does01:13 – LinkedIn as a distribution channel02:02 – The guest’s entrepreneurial journey03:14 – Origin story of FletchPM & the meaning behind the name05:30 – What is a value proposition?06:48 – Common mistakes B2B founders make10:24 – Specificity vs Scale: The 80/20 of niche selection12:06 – The importance of consistency in marketing14:33 – Distribution > Product16:47 – Building a founder brand18:09 – Lessons from being a generalist23:08 – How often should startups revisit positioning?25:13 – What is product-market fit really?27:00 – Go-to-market fit vs solution fit30:36 – DIY positioning: When & how to run the exercise32:16 – Why founders should think like marketers34:06 – Leaving a 9-5 to build a consultancy36:06 – How the co-founders met and got specific39:14 – Building distribution through a niche market map43:52 – Co-founder dynamics & communication styles46:03 – Decision-making heuristics50:35 – Competitive positioning done right52:12 – Leaving the agency & scaling up54:12 – The 3 paths they considered after early success56:48 – How the positioning evolved over time59:00 – Pricing journey: From $300 to $10K1:01:59 – What clients really get out of working with them1:05:20 – Founders can't outsource their thinking1:07:40 – Building a 7-figure business through LinkedIn1:10:14 – Tips for writing better LinkedIn content1:12:49 – Authenticity vs persona1:14:11 – Best time to post on LinkedIn?1:18:05 – 3 must-have resources for B2B founders1:19:10 – FletchPM's tech stack1:20:21 – What keeps him up at night1:21:07 – One question for the next guest1:22:03 – Final plugs & where to reach out

In this episode, we sit down with the founder of TrulyMadly, India's most trusted dating app, to explore the startup journey, fundraising pitfalls, growth hacks, and how TrulyMadly is solving the trust problem in Indian online dating.We dive deep into:- Competing with global giants like Tinder and Bumble.- How compatibility scores and trust-based algorithms changed the game.- The dark side of fake profiles and how TrulyMadly tackled it.- Fundraising regrets and the decision to stay profitable.- Building a brand people actually trust in a highly sensitive market.Whether you’re a founder, product builder, or just curious about the business of love.This episode is packed with insights. Watch the full episode on  @FundsAndFounders  Timestamps:00:00 - Intro01:23 - The European backpacking trip that changed everything03:39 - Early career: From payments to dating06:35 - Building a product for Indian singles09:03 - How TrulyMadly started12:10 - Solving the dating trust problem in India15:12 - TrulyMadly vs Tinder: What makes us different17:30 - Revenue vs Users: The real startup pivot20:02 - Fundraising mistakes & hard lessons22:25 - Branding, logo, and product-market fit25:47 - Compatibility scoring & TrulyMadly algorithm28:10 - Marriage success stories from TrulyMadly30:17 - Why TrulyMadly charges users (and why it works)33:50 - Dealing with fake reviews and app store ratings36:04 - The importance of frugal innovation39:00 - Final thoughts, rapid fire & what’s next

In this episode of Funds and Founders, we sit down with Cody Anderson — early employee at Carta, investor, limited partner, and now the founder of Tommy — a startup revolutionizing shared homeownership. Cody shares his journey from growing up in a small business family in Minneapolis to building a career at Carta, why he believes co-ownership is the future of real estate, and what it really takes to start your own company today. We also dive deep into the realities of founder life, angel investing, social media pressures, and staying sane while building ambitious projects. Topics Covered: - Cody’s early exposure to entrepreneurship - Lessons from 8 years at Carta - Why co-ownership is a game-changer - How to navigate early startup roles - Dealing with perfectionism and founder mental health - Angel investing, incentives, and how venture capital really works - Building Tommy: from idea to action Timestamps: 00:20 - Cody’s entrepreneurial roots in Minneapolis 03:25 - Lessons from parents’ small businesses 04:40 - Moving to San Francisco: the leap from hometown 05:46 - Early sales job and deciding to move 07:10 - Joining Carta at 30 employees and $1M revenue 08:00 - Why Cody chose an early-stage startup 10:15 - Staying 8 years at Carta: purpose and mission 13:24 - Scaling Carta’s network through data-driven expansion 16:26 - Lessons on network effects and scaling 20:38 - Leaving Carta and early thoughts on Tommy 23:00 - First steps: building Tommy’s website and lead-gen tools 24:20 - Using AI and technology in real estate 27:30 - Social media vs. real productivity for founders 36:00 - Why understanding incentives is crucial for founders 38:00 - Lessons from venture capital and fundraising 40:00 - Building Tommy: Marketing challenges and opportunities 43:00 - Messaging, SEO, and customer education 45:00 - Testing content: blogs, social media, videos 48:00 - Future ideas: AI in conflict resolution and co-ownership 54:00 - Cody’s startup tech stack and favorite tools 57:00 - Advice for early entrepreneurs 59:00 - Final thoughts: build a life you love Watch the full episode @FundsAndFounders for more deep dives with founders shaping the future. 🚀 #startups #founderstory #entrepreneurship #realestate #fundsandfounders #ai #business