#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson
Release Date: 07/18/2025
#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
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
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
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
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
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
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
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
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
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...
info_outlineChris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and developed the Salesmsg product for a different SMS use case that served his previous customers.
Salesmsg now provides secure SMS texting across all departments in the company, integrated directly with Hubspot CRM. It includes voice calling, sophisticated SMS automation, opt-in management, analytics, and deep CRM integration.
Salesmsg has grown rapidly, exceeding $10 million in revenue with 65 employees, leveraging its deep integration with HubSpot and promoting through agency and affiliate partners. The company is independent and has no outside investors.
Quote from Chris Brisson, the CEO and founder of Salesmsg
“In 2015, I wrote this post to our email list of 36,000 called The Death of Call Loop. I shared the story of how I created a business I secretly despised. We were shackled and couldn't innovate. I wanted to create a better company and reinvent the business from the ground up. My second chance startup became Salesmsg.
“When you start a company and it stalls, at what point do you say It's not the horse to ride? I've been there. At what point do you say, Enough is enough? Because you're only going to get older.
“I've always gone after solving problems, but some problems were worthy of the adventure, others not so much. Make sure you're choosing the right opportunity because it will take seven years of your life. And you can pivot along the way, but man, you want to find out early if it's worthy of the adventure.”
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