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#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda

Practical Founders Podcast

Release Date: 11/21/2025

#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock show art #181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock

Practical Founders Podcast

Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in the dental industry managing his family’s dental lab business. BoomCloud now does about $3M in ARR with roughly 600 dental practices and an 11-person team. The company helps dentists replace insurance-driven revenue with subscription-based patient memberships, creating higher margins and more predictable cash flow. BoomCloud has been profitable since 2016 and continues to...

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#180: AI Is Not Killing Vertical SaaS - It’s Practical Leverage - Deepak Sindwani  show art #180: AI Is Not Killing Vertical SaaS - It’s Practical Leverage - Deepak Sindwani

Practical Founders Podcast

Deepak Sindwani is Managing Partner at , an active growth equity firm backing bootstrapped and lightly funded SaaS founders. They work with practical founders who’ve built profitable businesses to $5–$20M ARR and want help growing without VC pressure or losing control. Wavecrest invests in vertical SaaS companies growing 30–60% annually, typically profitable or breakeven. They help founders scale sales, pricing, analytics, and leadership teams while staying capital efficient. Investments are usually $10–$30M total, with founders often taking some liquidity while continuing to lead....

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#179: Don’t Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke  show art #179: Don’t Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke

Practical Founders Podcast

Tighe Burke is the founder of , a boutique executive search firm that helps SaaS founders replace themselves as CEO without selling their companies. After years in large executive recruiting firms, Tighe built a practice focused on founders who want their business to keep growing while they step back from day-to-day leadership. Tighe works with profitable software companies typically in the $5M–$50M revenue range, helping founders hire experienced and scrappy operators who have already scaled businesses through the next phase. His team has completed more than 75 executive searches, often...

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#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald show art #178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald

Practical Founders Podcast

Dan MacDonald is the founder and CEO of , based in Edmonton, Canada. He didn’t start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online safety systems. That shift eventually became a long-term bet on a “un-sexy” problem that companies can’t ignore.  Today, BIS Safety serves more than 2.5 million users across high-risk industries like construction, mining, transportation, and energy. The company generates roughly $25M CAD in annual revenue, employs about 200 people globally, and runs one of the stickiest SaaS platforms...

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#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler show art #177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler

Practical Founders Podcast

Robin Eissler is the founder and CEO of , a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club and discovered a messy problem run with spreadsheets, emails, and manual accounting. She decided to build a single system that could actually handle it. BoosterHub now serves nearly 600 booster programs, representing over 100,000 users. With just two full-time employees and a small dev team, the company processes more than $40M in transactions across payments, fundraising, merchandise...

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#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head show art #176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head

Practical Founders Podcast

As the year winds down, I want to share an end-of-year message for practical SaaS founders who want to make better progress in 2026. Based on my recent conversations with more than 40 CEOs in my Practical Founders peer groups, it’s clear that growth rates alone don’t define whether it was a “good” year. Founders experienced very different outcomes—and very different feelings about them. In this episode, I walk through five practical questions I believe founders should ask as they look ahead to 2026 (or their next quarter). These questions focus on whether you’re working on the...

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#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh show art #175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh

Practical Founders Podcast

Dave Hersh, co-founder and former CEO of Jive Software, shares the real story behind bootstrapping Jive to $12M in revenue before raising venture capital and scaling aggressively. He explains how fear, comparison, and the pressure to “go big” drove him to abandon his profitable core business and pursue a new upmarket strategy that ultimately cost the company its soul.  After growing to $60 million, Jive eventually went public, but not without internal strain, personal turmoil, and ultimately the realization that the company had drifted away from what made it successful.  Dave...

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#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho show art #174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho

Practical Founders Podcast

Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh built the first version himself, validated demand quickly, and landed early customers by doing demos and hands-on support.  Referral Rock has grown to roughly 500 customers, 20 team members, and about $3M in annual revenue. The company scaled through strong inbound SEO, founder-led sales, and a high-touch onboarding model for B2B businesses that value referrals. Over...

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#173: From COVID Boom to Bootstrap Mode: Hubilo’s Refounder Story - Shailesh Hegde show art #173: From COVID Boom to Bootstrap Mode: Hubilo’s Refounder Story - Shailesh Hegde

Practical Founders Podcast

Shailesh Hegde is the CEO of , a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors.  When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams. They shifted from large in-person event organizers to...

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#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel show art #172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel

Practical Founders Podcast

Raju Patel founded over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality. His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams.  Today eShow has 125 employees, more than 14 integrated modules, and supports hundreds of events each year for 300+ customers, including large...

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More Episodes

Dharshan Rangegowda, founder of ScaleGrid, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to helping developers manage MongoDB, Redis, and Postgres on the cloud, bootstrapping the business from scratch.

ScaleGrid grew steadily through product depth, technical support, and Dharshan’s mastery of SEO—becoming the top organic result for many key searches. The company expanded into multiple database engines, added a distributed engineering team, and reached 20 employees by 2021, serving both SMB developers and some enterprise teams. 

Dharshan sold a majority stake to Spotlight Equity Partners during the pandemic after receiving an unsolicited offer, later stepping out of day-to-day operations while remaining on the board. 

In this conversation, Dharshan shares hard-earned lessons about product-led growth, support as strategy, SEO as a long-game advantage, and how bootstrapped founders can build meaningful outcomes in massive markets. 

Key Takeaways

  • SEO Power: SEO remains a long-term growth engine for bootstrappers because big VC-backed companies rarely have the patience to compound it.
  • Support as Strategy: Deep, responsive technical support became ScaleGrid’s differentiator and directly informed product innovation and content.
  • Start at the Edges: Enterprises won’t buy from a one-person startup, but edge users with urgent problems will — and they become your early beachhead.
  • Bootstrap Constraints: Founder over-frugality can limit growth; strategic delegation and early team building prevent burnout and plateauing.

Quote from Dharshan Rangegowda, founder of ScaleGrid

“You can't take random people and make them an entrepreneur. You have to want to be an entrepreneur and want to be on your own. You have to enjoy the freedom and the risk and the upside that comes with it and the unmitigated downside as well. You have to accept and be comfortable with it. 

“You want to be on your own so you can try things. You are constantly looking at problems and new solutions. You want to be around people who like that sort of process: Here's a new problem and here's a new solution. 

“But the most important thing you have to do as an entrepreneur is you have to add value to your customers. And most people forget that.”

Links

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This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.

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