In this insightful conversation, Rebecca Shostak, co-founder and chief brand officer of Flodesk, shares her impressive journey of growing the email marketing platform to over $30M in annual recurring revenue—completely bootstrapped. She delves into vital topics like product design, the innovative unlimited pricing model, and maintaining profitability without outside funding. Rebecca also highlights the significance of understanding challenges before hiring and discusses how AI is enhancing their services. Prepare for an inspiring tale of entrepreneurship and creative problem-solving!

Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry.   After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second company, Strety.   Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company. Links Brian Dosal on LinkedIn BrightGauge website Strety on LinkedIn Strety website Entrepreneurial Operating System (EOS) website Traction book by Gino Wickman Anything You Want book by Derek Sivers   The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Dave Yuan, founder of Tidemark Capital and investor in successful vertical SaaS companies like Toast and ServiceTitan, shares invaluable insights on scaling strategies. He discusses the significance of control points in thriving markets and the evolving landscape shaped by AI. Dave emphasizes the importance of community among founders, innovative growth frameworks, and adapting to challenges posed by new technologies. He urges vertical SaaS entrepreneurs to harness AI thoughtfully to enhance their offerings and stay competitive.

Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support.  SimpleClosure has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important steps of a winddown, including legal, regulatory, employees, investors, intellectual property, customers, data, and more.  In this episode, Dori shares the key considerations for SaaS founders who have run out of VC funding or need to shut down their companies for other reasons.   Quote from Dori Yona, CEO of SimpleClosure “The biggest thing for software startup founders and CEOs is to move fast. Your time is your biggest resource in life as an entrepreneur, whether you’re venture-backed or bootstrapping. You’re spending your time,  you’re spending your energy, you’re spending the best years of your career. “So move fast, learn fast, test fast, iterate quickly, grow fast, fail fast. Ultimately, when you’re building your own business, you’re sacrificing an easy, convenient, cushy job anywhere else to take this risk. “The faster you can grow, learn, build, and fail, the better. It’s ultimately to your advantage to make the most of your time. Our time is our most expensive resource.” Links Dori Yona on LinkedIn SimpleClosure on LinkedIn SimpleClosure website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Howard Gottlieb, founder of Read-A-Thon, launched a reading-based fundraising platform that has helped over 4000 schools raise over $30 million. He discusses the explosive growth during COVID, which propelled his company from 40% to 150% yearly growth. Howard shares insights on selling to private equity, focusing on effective negotiation and the emotional challenge of transitioning leadership. He also reflects on the vital blend of luck and hard work in entrepreneurship, emphasizing the importance of humility and strategic wealth management in his journey.

Richard Change, co-founder and CEO of PFA Solutions, shares his inspiring journey of bootstrapping a software company that revolutionized carry and compensation management for private equity firms. He discusses the complexities of private equity integration post-acquisition and reflects on key operational changes. Richard emphasizes the shift from consulting to SaaS, illustrating how trust and credibility were crucial in navigating the private equity landscape. The conversation highlights the importance of strategic support beyond funding and the challenges of maintaining independence in a larger organization.

Rachit Khator, the founder and CEO of Stackby, shares his inspiring journey from working in a corporate venture firm to launching a successful no-code platform that empowers users without technical backgrounds. He discusses the strategic decisions that fueled Stackby’s growth to 75,000 customers while competing against well-funded rivals. Rachit reflects on the entrepreneurial spirit in India's smaller cities, the importance of customer feedback, and innovative growth strategies, all while navigating the challenges of building a sustainable business in a competitive landscape.

Joe Hyrkin, former CEO of Issuu, shares insights from leading the content publishing platform to $30 million in revenue before its acquisition. He discusses the balance of profitable growth and debt management in the tech landscape. Joe highlights the transformation from print to digital marketing, and the importance of building long-term relationships over chasing venture capital. Additionally, he emphasizes sustainable practices and strategic planning needed for success in an evolving market, showcasing how to thrive through challenges.

Brian Hamilton, a fintech pioneer and founder of Sageworks, shares his compelling entrepreneurial journey. He discusses the evolution of Sageworks from struggles to success, emphasizing the importance of bootstrapping and innovation. Hamilton highlights the impact of location on entrepreneurial spirit, contrasting Chicago and North Carolina. He also advocates for entrepreneurship as a pathway for ex-inmates, urging for systemic changes to support reintegration. The conversation delves into the emotional challenges of business ownership and the balance between financial success and personal fulfillment.

Scott Desgrosseilliers, founder and CEO of Wicked Reports, shares insights from his journey in building a bootstrapped SaaS company focused on marketing attribution for SMBs. He discusses the complexities of identifying effective marketing strategies, the importance of high-quality data, and the potential pitfalls of VC funding. Scott emphasizes resilience and strategic decision-making in overcoming challenges like near-failure moments, navigating SaaS financing, and fostering sustainable growth while enhancing customer engagement through data-driven insights.