#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald
Release Date: 01/09/2026
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...
info_outlinePractical 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....
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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...
info_outlinePractical 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_outlineDan MacDonald is the founder and CEO of BIS Safety Software, 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 you’ll find—with less than 1% annual logo churn.
After nearly 20 years of bootstrapped growth, Dan is beginning a staged exit, starting with a minority secondary sale and planning a control transaction in a few years. Along the way, he shares hard-earned lessons about product obsession, compounding customer retention, and why steady execution beats hype.
Key Takeaways
- Extreme Retention Matters — Less than 1% annual churn created compounding growth without aggressive sales spending.
- Product Over Sales — BIS focused on usability and depth first, letting word-of-mouth drive most early growth.
- Customer-Funded Start — Early customers paid to build the first LMS, avoiding dilution and premature fundraising.
- Long Bootstrap Reality — The first decade involved no salary, deep personal risk, and constant financial pressure.
- Enterprise Power, End User Simplicity — Power users get depth, while users see an interface designed to feel effortless.
Quote from Dan MacDonald, Founder and CEO of BIS Safety Software
“So at that time when I started the business, there was an awakening kind of moment of realization. It hit me big. I'm reading hundreds of business books and reading about Bill Hewlett, Dave Packard, Sam Walton, and many others.
“I'm listening to the things they're saying, the ways they're thinking, And all I'm thinking is, my God, they think like me, they're just like me, they're normal people, they're just like me. And that was kind of the first awakening realization to say, they're not superhuman!
That gave me the confidence to build the business and believe in the future. I never thought there's a pot of gold at the end of the rainbow it was never about the money. It was just some burning thing inside me that just I need to do this.I was just driven to do to do this. I felt like it was just this is what I'm meant to do.”
Links
Podcast Sponsor – Lighter Capital
This podcast is sponsored by Lighter Capital.
In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.
Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.
Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.
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.
Practical Founders CEO Peer Groups
Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.