Practical Founders Podcast

Jordon Comstock, founder and CEO of BoomCloud who built a profitable vertical SaaS for dental memberships, talks systems-first scaling and bootstrapped discipline. He covers hiring mistakes, narrowing an ideal customer, AI-augmented content and product work, and building durable, profitable growth instead of chasing fast exits.

Deepak Sindwani, Managing Partner at Wavecrest Growth Partners, champions capital-efficient vertical SaaS founders. He discusses how practical businesses, not reliant on VC pressure, are thriving with AI, emphasizing that AI enhances rather than replaces existing solutions. Deepak highlights the significance of founder liquidity in decision-making and the unique defensibility of vertical SaaS through deep industry knowledge. He also explores tailored support strategies over rigid playbooks and the promising future of predictive analytics driven by shared datasets.

Tighe Burke, founder of SRCH Partners and expert in executive searches, discusses how SaaS founders can step back by hiring a CEO instead of selling. He shares insights on identifying founder readiness, the importance of profitability for hiring top operators, and how this strategic move can multiply a company's value. Tighe explains the ideal backgrounds for CEOs, compensation structures, and offers red flags to watch for during the transition. Ultimately, he encourages founders to envision their future roles to make the best decision for their businesses.

Dan MacDonald, founder and CEO of BIS Safety Software, shares his journey from retail to creating a bootstrapped safety management platform catering to high-risk industries. He discusses the incredible 99% retention rate that fuels their growth, emphasizing a product-first approach over aggressive sales. Dan reveals the importance of customer-funded development and the financial sacrifices that shaped his company. With AI integration on the horizon, he highlights the potential productivity boosts while underscoring the value of persistence and community support for founders.

Robin Eissler, founder and CEO of BoosterHub, shares her journey from private jet broker to building a vertical SaaS for high school booster clubs. She discusses how her all-in-one platform streamlines payments, fundraising, and accounting, serving nearly 600 clubs. With a tiny team, Robin reveals how they handle seasonal revenue swings and embrace sticky customer relationships. She highlights the advantages of founder-led marketing and using AI for efficiency, all while remaining bootstrapped and on the path to profitability.

As the year ends, founders are encouraged to rethink success beyond growth rates. The focus should be on tackling hard initiatives that truly drive progress. Evaluating priorities and resisting shiny-object syndrome is crucial for concentration. Founders need to identify necessary changes for the coming year and the support required to navigate challenges. It's essential to have a cushion for setbacks, while the narrative surrounding progress can significantly impact morale. Embracing these insights leads to steady forward momentum.

Dave Hersh, former co-founder and CEO of Jive Software, dives into the complex psychology of founders and how it impacts their companies. He reveals how fear and comparison led him to abandon a successful core business in pursuit of rapid growth. Dave emphasizes the importance of addressing subconscious patterns that cause stagnation and how human-centered strategies can revitalize underperforming SaaS businesses. He shares insights on scaling wisely, the value of emotional connection, and his journey through personal recovery to better support founders.

Josh Ho, Founder and CEO of Referral Rock, shares his journey from solo developer to leading a profitable SaaS company serving SMBs. He discusses the importance of charging early and adapting pricing models to fit customer needs. Josh highlights the power of high-touch onboarding and founder-led demos as growth strategies. He also addresses the challenge of product complexity and emphasizes a focus on simplicity and core functions. Most intriguingly, he reframes revenue plateaus as puzzles to solve, encouraging a mindset of continual improvement and enjoyment in business.

Shailesh Hegde, CEO and refounder of Hubilo, shares his journey leading the company through a tumultuous post-COVID landscape. He discusses pivoting Hubilo from virtual events to a B2B-centric webinar platform, emphasizing AI-driven content repurposing. Shailesh delves into the challenges of returning investor capital and adopting a bootstrap mindset for survival. He also highlights strategic choices in transitioning to mid-market clients and the exciting acquisition by BrandLive, while reflecting on the lessons learned about leadership and market adaptation.

Raju Patel, the Founder and CEO of eShow, shares insights from his 25+ years in the event management SaaS industry. He explains how he built a niche focusing on complex association events, enabling steady growth without big bets. Raju discusses the evolution of his platform, emphasizing passion over profit, and the importance of deep modular features. He reflects on transforming from a founder-doer to a CEO, highlighting challenges like churn and the impact of COVID. Raju also reveals plans for hybrid events and integrating AI into their systems.