The Peel with Turner Novak

Jonathon Barkl, Co-founder and CEO of Air Garage, discusses the business model of parking, the outdated nature of the $131 billion parking industry, and how Air Garage increases parking lot profitability. He shares the inspiration behind Air Garage and the sales lessons learned. Jonathon also talks about securing funding, dynamic pricing in parking, and the impact of parking on cities.

Dan Lorenc, Co-founder and CEO of Chainguard, talks about the software supply chain and the vulnerabilities it poses. He discusses the history of open source software, the moment they decided to start Chainguard, and why they started selling consulting services before building a product. Dan also shares insights on their marketing strategy, raising funding, and the challenges and risks in open source software.

Guest Nichole Wischoff shares her journey from growing up on food stamps to founding Wischoff Ventures, a Pre-Seed and Seed firm. Topics include studying abroad in Belgium, falling in love with running, starting a bakery in Spain, getting her first job in fintech, and raising her first $20m fund with the help of Lee Fixel and Chad Byers.

Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox. — Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors. — Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3FoYm52 — In this episode, we discuss:• Why Waseem’s building a startup that does your accounting• The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders• When startups should build something themselves and when to outsource• All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox• How to avoid “fake work”• How to get ROI from conferences• His disastrous first ever meeting with a VC• Why the best fundraising advice is to build a business that doesn’t need to raise money• “Companies are bought, not sold” and his framework for startup M&A• Why it’s a mistake to build your startup just to be acquired• Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet• Why tech-enabled service businesses are so hard to scale• How Pilot got its first customers• Pilot’s unique approach to raising its Seed round• The initial scare when raising their Series A• Why its Series B was half of what they could have raised —Where to find Waseem: • Twitter: https://twitter.com/waseem • LinkedIn: https://www.linkedin.com/in/wdaher • Newsletter: https://waseem.substack.com/ — Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak — Production and distribution by: https://www.supermix.io — For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Vlad Magdalin, Co-founder and CEO of Webflow, discusses the history of web design, empowering non-engineers with Webflow, the evolution of technology in web design, his journey as a refugee to the US, and the challenges and adaptations in building a successful startup.

Keith Rabois, Co-founder and CEO of OpenStore, discusses the problems in ecommerce, why Instagram Shopping and Wish failed, contribution margin in startups, and what he looks for in founders. He also shares his thoughts on AI startups, his favorite interview questions, and the reasons behind moving to Miami.

Natasha Vernier, Co-founder and CEO of Cable, discusses the $4 trillion market of financial crime, highlighting the prevalence of crime for financial gains and the difficulty in stopping it. She explores the increase in financial crime on crypto rails and the growing synthetic ID fraud. Natasha also shares her experience joining Monzo, building Cable to help regulatory and financial crime teams, and raising funds for the startup.

Alex Bouaziz, Co-founder and CEO of Deel, shares the journey of growing Deel from zero to $300M+ ARR in four years. Topics discussed include the initial insight around remote work, pivoting before YC demo day, Deel's remote-first approach, fundraising strategies, and the importance of building the right board and selecting committed board members.

Semil Shah, the founder of Haystack, shares insights from his journey in venture capital, detailing how he built the firm from the ground up. He discusses the emotional trials of fundraising, the importance of relationships, and key strategies for investing in early-stage companies. Semil highlights the evolution of investor expectations and the challenges of maintaining communication in a changing landscape, reflecting on mistakes made along the way. His story emphasizes the delicate balance between personal and professional responsibilities in the competitive world of venture capital.

Sean Frank, CEO of Ridge Wallet and known as the 'Einstein of Ecommerce', discusses topics such as the challenges of selling wallets, Ridge's 80% gross margins, the decision to not raise venture capital, hiring a new CEO, marketing strategies including Twitter advertising and influencer sponsorships, the future of women's return rates in fashion, vertical integration through investing in a watch manufacturer and building a factory, the importance of core competency, Ridge's tech stack, and the challenges and potential future of e-commerce penetration.