Shows
Funded with Alex WittenbergHow Campfire Raised $100M+ While Doubling Revenue Six Quarters Straight | John Glasgow, CampfireIn the latest episode of Funded, Campfire CEO John Glasgow shares how he raised $103.5M across three rounds in under a year while running every sales call, closing the books as CFO, and building one of the fastest-growing AI-native ERPs in the market.John breaks down his fundraising strategy: stacking all investor meetings into two-week windows, choosing board members he'd worked with before, and managing back-to-back rounds while the business was exploding.
2026-02-1154 minFunded with Alex WittenbergWhy Market Size Trumps Everything In VC Deals | Jesse Robbins, HeavybitJesse Robbins from Heavybit breaks down what VCs actually look for when evaluating early stage startups and why most founders get it completely wrong.Jesse reveals the brutal truth about funding stages - pre-seed typically needs zero revenue but credible design partners, seed stage requires $500K to $1.5M in revenue, and Series A demands $1.5M to $3M. He explains why market size is the ultimate arbiter of whether Heavybit will invest, even if they love the team and product.The conversation dives deep into founder evaluation, where Jesse looks for personal...
2026-01-281h 07
Funded with Alex WittenbergWhy Market Size Trumps Everything In VC Deals | Jesse Robbins, HeavybitJesse Robbins from Heavybit breaks down what VCs actually look for when evaluating early stage startups and why most founders get it completely wrong.Jesse reveals the brutal truth about funding stages - pre-seed typically needs zero revenue but credible design partners, seed stage requires $500K to $1.5M in revenue, and Series A demands $1.5M to $3M. He explains why market size is the ultimate arbiter of whether Heavybit will invest, even if they love the team and product.The conversation dives deep into founder evaluation, where Jesse looks for personal...
2026-01-281h 08Funded with Alex WittenbergStrategic Confidence in the Seed Funding Round | Henry LeGard, VerisoulIn this episode of Funded, Alex Wittenberg sits down with Henry LeGard to explore his fundraising journey for Verisoul, a company dedicated to detecting fake accounts and bots. Henry shares valuable insights on the challenges he faced and strategies he employed during a seed round. In this conversation, Henry recounts a creative yet ultimately ineffective marketing stunt involving Mardi Gras cakes aimed at attracting potential clients. Alex and Henry deep dive into constructing a compelling narrative that resonates with investors by focusing not just on traction but also on the size of the market opportunity and the...
2026-01-2255 minFunded with Alex WittenbergThe Urgent Pain Point Test Every Startup Must Pass | Arun Penmetsa, Storm VenturesStorm Ventures partner Arun Penmetsa reveals exactly how his firm evaluates early stage B2B software startups and what separates companies with staying power from those destined to flame out. With 25 years of experience and investments across 6 funds, Storm specializes in helping companies transition from founder-led sales to scalable go-to-market teams.Arun breaks down Storm's 3-stage investment process and shares the key traits they look for in founders. He explains why team comes first, followed by market urgency, and how the AI boom has complicated traditional evaluation metrics. The conversation dives deep into what makes AI companies...
2026-01-2252 minFunded with Alex WittenbergThis $55M Secret is Changing How Finance Teams Work
| Ali Hussain, TabsFresh off announcing their $55M Series B led by Lightspeed Venture Partners, Tabs CEO Ali Hussain reveals how AI is transforming the finance function. Ali shares the founding story behind Tabs - how his team spent 3 months having 8 calls per day with finance professionals to deeply understand revenue accounting pain points.The conversation explores Tabs' new AI agents for billing and collections, plus Ali's 4-step framework for building production-ready AI agents in finance. He explains why finance teams have historically blocked new revenue streams and how modern tools are changing that dynamic.Ali also discusses...
2026-01-2259 minFunded with Alex WittenbergThe Secret Signal VCs Look For In First Time Founders | Eric Bahn, Hustle FundEric Bahn reveals the framework Hustle Fund uses to evaluate 1,000+ monthly pitches and select just 7 investments. From building Beat The GMAT to becoming a top early-stage VC, Eric breaks down the counterintuitive signals that separate future unicorns from the pack.Listen in as Eric shares real examples from Hustle Fund's 620-company portfolio.
2026-01-2257 minFunded with Alex WittenbergFrom 130 Rejections to 4M Seed Round Success | Scott Hickle, ThroneScott Hickle is building Throne, the world's first wearable for your toilet that he calls "Whoop for your poop." This AI-powered device clips onto your toilet and analyzes what's in the bowl to provide health insights straight to your phone, with the ultimate vision of becoming a smoke detector for colon cancer.What makes this story incredible is Scott's resilience in fundraising for a startup at the intersection of three notoriously difficult sectors for VC funding: consumer, healthcare, and hardware. He pitched over 130 investors to raise his 4M seed round, with some literally telling him in the...
2026-01-2251 minFunded with Alex WittenbergInsights From a Founder Who Raised $95M in Just 11 Days | Nicolas Kopp, RilletNicolas Kopp, Founder and CEO of Rillet, shares how he raised $95 million across two funding rounds in just 11 days of actual fundraising work. After building an AI-native ERP system in stealth for nearly two years, Rillet announced a $25 million Series A led by Sequoia in May, followed by a $70 million Series B led by Andreessen Horowitz just three months later.The company doubled ARR in 12 weeks after their Series A, supporting over 200 companies with an unprecedented NPS score of 71 for accounting software. Nicolas explains the strategic decision to take a preemptive Series B offer rather than wait...
2026-01-2256 minFunded with Alex WittenbergInvesting in Companies You Can't Clone | Jed Katz, Javelin Venture PartnersIn this episode of Funded, we sit down with Jed Katz, Managing Director at Javelin Venture Partners. With over 15 years and more than 120 deals under his belt, Jed offers a raw and honest look at what it takes to get funded in today's dynamic market.Jed reveals Javelin's unique, sector-agnostic approach, explaining that they invest in ideas they would be passionate about building themselves. As former founders, they prioritize scrappiness and intellectual honesty in a team, viewing these traits as key indicators of success. He shares a candid look at their due diligence process, emphasizing that while...
2026-01-2246 minFunded with Alex WittenbergBuilding Billion Dollar AI Businesses | Rudina Seseri, Glasswing VenturesIn this episode of Funded, Alex Wittenberg sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to discuss what it really takes to build and scale a successful AI startup. Rudina emphasizes the distinction between building a strong product and creating a successful business, highlighting the complexities of early go-to-market strategy, landing initial flagship customers, and getting pricing right. Both she and Alex explore how early foundational decisions—especially operational shortcuts—can add up as operational debt, potentially causing bigger problems as a company begins to scale.The conversation goes into depth on Glasswing Vent...
2026-01-2259 minFunded with Alex WittenbergFounder Mistakes, Market Sizing, and Pitch Tips | Mark Volchek, Las Olas Venture CapitalIn this episode of Funded, Alex sits down with Mark Volchek, founding partner at Las Olas Venture Capital (LOVC). Mark brings a wealth of experience to the discussion, having previously co-founded Higher One—a fintech company he helped lead from inception through IPO. His extensive background as both an operator and investor shapes Las Olas’s approach and commitment to supporting founders beyond just providing capital.The conversation dives deep into Las Olas Venture Capital’s investment philosophy, focusing specifically on early-stage B2B software startups. Mark explains that while market size and demand are crucial, LOVC priori...
2026-01-2248 minFunded with Alex WittenbergHow to Think About Seed Stage Investing and Fundraising | Nick Adams, DifferentialIn this first episode of Funded, Alex Wittenberg, CEO of airCFO, sits down with Nick Adams, co-founder and Managing Partner at Differential Ventures, to demystify the venture capital fundraising process for early-stage founders. Alex and Nick provide practical, actionable insights for startup founders looking to tackle their next fundraise. Nick brings both deep investment experience and operational expertise in AI, machine learning, and data infrastructure to the discussion. With Differential Ventures having raised over $100 million across three funds and making over 40 investments, Nick is able to offer a rare perspective from both sides of the table.
2026-01-2254 minFunded with Alex WittenbergPositioning Against ChatGPT and Fundraising Strategies | Taher Hassonjee, DocDraftIn this episode of Funded, Alex Wittenberg sits down with Taher Hassonjee, founder of DocDraft, to dive deep into the realities of early-stage fundraising for startups. This episode focuses on DocDraft’s journey, from the early decision to be an “AI-first” legal tech company to raising a $1.5 million pre-seed round, led by Harlem Capital in mid-2023.Taher walks listeners through the granular details of the fundraising process, sharing candid advice and tactics. He discusses building an investor list of 50-70 firms, the importance of leveraging personal networks versus relying on cold outreach, and tactics for keeping track of inv...
2026-01-2246 minFunded with Alex WittenbergHow To Impress On Your First Call | Kristina Chapple, 11 Tribes VenturesIn this episode of Funded, Alex welcomes Kristina Chapple, General Partner at 11 Tribes Ventures, for a candid conversation about reshaping early-stage venture capital. Kristina, recently recognized on Forbes 30 Under 30 and Chicago Innovations 25 Under 25 lists, offers insight into how 11 Tribes goes beyond financial metrics to focus on the well-being and resilience of founders. Rather than just measuring success through exit valuations or growth rates, Kristina highlights the importance of evaluating founder outcomes, such as the health of personal relationships, mental and physical health, and the sustainability of the entrepreneurial journey. Throughout the episode, Kristina and Alex explore the...
2026-01-221h 11Funded with Alex WittenbergSecrets from Subscript's Fundraise Journey | Sidarth Kakkar, SubscriptIn this episode of the Funded, Alex sits down with Sidharth Kakkar, the founder of Subscript, to discuss his journey in raising a $15 million Series A round. The conversation spans various aspects of fundraising, including Sidharth's approach to crafting a compelling narrative for investors, the importance of finding believers rather than trying to change investment perspectives, and the nuances of the delicate relationship between a founder and investors.Throughout the discussion, Alex and Sidharth emphasize the iterative nature of developing a fundraising strategy and the need to leverage the founder community for guidance. Sidharth's background as a...
2026-01-2146 minFunded with Alex WittenbergHow to Scale to $100M ARR with a 3-Person Finance Team | Riya Grover, SequenceRiya Grover, Cofounder and CEO of Sequence, breaks down how AI-powered revenue automation is transforming finance operations for high-growth startups. Companies like Cognition, Deel, and MoonPay are scaling to 9 figures with finance teams of just 3-5 people—and Riya explains exactly how they're doing it. Riya also reveals the behind-the-scenes story of Sequence's Series A fundraise: how they landed multiple term sheets in just 3 weeks and what investors really want to see beyond the "AI" buzzword. She shares why human-in-the-loop design is the difference between AI that works and AI that creates chaos, plus her framework for bu...
2026-01-2158 min
Lay of The Land[GREATEST HITS] #23: Justin McLoughlin (airCFO)Justin McLoughlin — Founder & CEO of airCFO — on building a bootstrapped company, scaling a professional services organization, the future of work, the importance of taking care of your employees, and finance!Justin McLoughlin is a midwesterner who fell in love with the tech startup scene and turned entrepreneur when he realized that when other people start startups, payroll, back-office management, account reconciliation, taxes, and general accounting is not what they have in mind.Justin started airCFO to deliver entrepreneurs and growing companies peace of mind by taking ownership of these accounting responsibilities — maintaining the books so the...
2023-06-2948 minLay of The Land#123: Tory & Michael Waxman (Sundays)Tory and Michael Waxman — the founders of Sundays (>$14 million raised, Cleveland-based) — on building Sundays for Dogs to become a leading dog food brand offering the first human-grade, air-dried dog food, made with 100% all-natural ingredients, that is healthier than kibble, but easier than refrigerated foods since it doesn’t require a freezer, prep, or clean-up.In pursuit of their mission to make it easier to be an awesome dog parent and feed millions of dogs, Tory and Michael have grown the business to offer modern dog parents everything they’re looking for including quality, taste, convenience, and affordab...
2023-06-221h 00Lay of The Land#122: Dom Raban (Xploro)Dom Raban — Founder and CEO of Xploro®While originally founded in the UK, Xploro has recently established its headquarters here in Cleveland accompanying the closing on over $1.7mm in funding in a round led by local investors including Comeback Capital, University Hospitals Ventures and JumpStart Ventures! Xploro is an award-winning and clinically validated health information platform that uses augmented reality, gameplay, and artificial intelligence to deliver health information to young patients, in a way that makes them feel empowered, engaged, and informed, whilst having fun at the same time.By putting health information in the...
2023-06-1547 minLay of The Land#121: Michael Bruckman (Haima Therapeutics)Mike Bruckman, CEO of Haima Therapeutics.With a PhD in organic chemistry and additional training in biomedical engineering and management, Mike joined the founding team at Haima as CEO in 2018 and has led their commercialization. Having brought in over $13mm in government funding to support their program over the last 5 years, Haima was the sole team selected by DARPA to receive funding in pursuit of manufacturing a fully-dried whole-blood product.Haima is a biopharma Cleveland-based company developing cell and platelet-inspired therapies for the treatment of bleeding and a variety of other blood-related ailments...
2023-06-0858 min
Accounting HighPuglia and the Preaccounting Superapp at ExpensiCon (feat. Expensify)Accounting High (aka Sons of CPAs Podcast)
Season 3 Bonus Ep | Recorded July 26, 2022
this is our reaction episode to one of the latest Expensify emails...
Okay. So if you are on Expensify's email list. You probably get emails from David Barrett all the time. He's known for sending really long opinionated irreverent emails... and we got an email directly from David with an invite to ExpensiCon.
now, now granted his emails come from David Barrett. It's got his picture on there in my Gmail, it always looks like a very personal email... ...
2022-09-2421 minLay of The Land#23: Justin McLoughlin (airCFO)Our conversation this week is with Justin McLoughlin — founder & CEO of airCFO — on building a bootstrapped company, scaling a professional services organization, the future of work, the importance of taking care of your employees, and finance!Justin McLoughlin is a midwesterner who fell in love with the tech startup scene and turned entrepreneur when he realized that when other people start startups, payroll, back-office management, account reconciliation, taxes, and general accounting is not what they have in mind.Justin started airCFO to deliver entrepreneurs and growing companies peace of mind by taking ownership of thes...
2021-05-1346 min
TaxValet: The Smart & Safe Small Business PodcastHow airCFO Helps Startups Manage Multi-State Income Tax RiskIn this episode, we talk about how airCFO helps fast-growing startups mitigate the risk of multi-state income tax. You can learn more about airCFO on their website.
2021-01-0709 min