SaaS Interviews with CEOs, Startups, Founders

Hootsuite was the social media darling of the 2017's by trouble started after a failed $750m IPO led by Goldman. Today, original founder Ryan Holmes and team have tasked new CEO Irina Novoselsky with leading the company from $200m to $400m. She says the old SaaS playbook is dead. Its working. The firm will hit $400m by Dec 2024.

Colin laucnhed the business back in 2012 and got stuck under $5m revenue until 2018. He 6x'd the business by 2022 to $30m in revenue and hit $70m in Septemer 2024. How did he do it? Hear the 9 mistakes he made that he think you should fight to avoid.

VoxPopMe has hit $6m in revenue. Wanting to avoid dilution, CEO Andy and the board rasied $750k from Founderpath. At the same time, Founderpath worked with the board to establish a new ESOP pool for management resutling in 10%+ more equity for leaders.

Tim, the founder of SaaS Group, shares his journey of acquiring 20 SaaS companies since 2018, leveraging his winnings from the Eyeo exit. He reveals insightful funding strategies, balancing personal investments, debt, and equity to grow his ventures. The discussion highlights the importance of navigating deal dynamics, managing customer churn, and understanding founder motivations. Tim also emphasizes the role of personal growth in professional success and the unique challenges of acquiring distressed companies, painting a vivid picture of the SaaS acquisition landscape.

Discover how ActiveCampaign soared to $100 million ARR by leveraging strategic growth marketing. Hear insights on the powerful role of AI and influencer partnerships in expanding brand visibility. Explore the importance of email engagement and the success stories behind notable SaaS companies. Delve into innovative lead generation tactics and performance-driven influencer strategies that attract thousands of trials monthly. Finally, uncover the significance of measuring success through metrics and embracing new media formats.

In this enlightening discussion, Alessandro Chesser, Co-founder and CEO of Dynasty, shares his extensive experience from his years as a sales executive at Carta. He explains why South Dakota is a key location for setting up trusts and the benefits of choosing between revocable and irrevocable options. Discover innovative tax strategies for entrepreneurs, including significant savings through qualified small business stock provisions. Chesser also emphasizes the importance of trusts for financial protection, especially for startups generating substantial revenue.

Tyler Denk launched Beehiiv after missing out on the ""Founder Money"" the MorningBrew team made when they exited. Today, his tool helps newsletter creators launch, grow, and monetize. The firm did $1.5m in revenue last month split between SaaS, ad revenue, and kickbacks on cross promoting newsletters. Can they hit $25m ARR this year?

Rebecca Shostak, founder of FloDesk.com, transformed a design background into a thriving email marketing tool, reaching $12 million in revenue in under 18 months. She shares insights on the powerful impact of community building and effective affiliate marketing strategies that drove user growth. Rebecca emphasizes the importance of understanding customer needs and minimizing reliance on traditional sales teams. With 80,000 subscribers, her approach to product development and customer feedback has paved the way for ambitious growth targets.

Discover the intriguing journey of Beamer's acquisition of Userflow and how it led to a remarkable $10 million in annual recurring revenue. Dive into the strategic insights on product alignment and cultural compatibility that made the deal a success. Learn about the essential communication strategies during due diligence and the challenges faced in post-acquisition integration. This tale provides valuable lessons for startups navigating the complex landscape of mergers and acquisitions.