Practical Founders Podcast

Robin Eissler is the founder and CEO of BoosterHub, 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 sales, and accounting. Annual contract value typically runs $1,500–$2,000 per customer, with strong retention and expanding usage. Still independently-owned and bootstrapped, BoosterHub is approaching $1M ARR and profitability. Robin shares lessons on building complex software with a tiny team, selling to volunteer buyers, surviving seasonal revenue swings, and why slow, compounding growth can create durable SaaS businesses without venture capital. Key Takeaways Tiny Teams Work - Two employees plus contractors can build serious SaaS with focus, systems, and modern tooling. Sticky Beats Big - Hundreds of small customers compound more reliably than a handful of enterprise deals. Seasonality Is Real Education-adjacent - SaaS must survive cash spikes and winter slowdowns without panic. Founder-Led Marketing - Consistent content from the founder still drives inbound growth in niche markets. All-In-One Wins in Verticals - Being the system of record makes churn low and customer value expand naturally over time. Quote from Robin Eissler, Founder and CEO of BoosterHub "The numbers are much better than what we projected. so we're starting to see that compounding effect is really what's happening is there's just enough users and enough people in the system that they're using more of the add-on products and we're processing more volume.  "So it's starting to have that compounding effect. And so I really just admitted to myself this month, like, I think we're seeing it.  "I think we're finally seeing it. I feel like, OK, maybe for me, it's almost that I can exhale. I've been holding my breath for four years, so maybe I can breathe." Links Robin Eissler on LinkedIn BoosterHub on LinkedIn BoosterHub website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. 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.

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 right hard things, what you're deliberately changing next, what help you actually need, whether you have enough cushion in the business, and the story you're telling yourself and your team about progress. This isn't about templates, quick-fixes, hype, or perfect planning. It's about making steady progress on the hardest, most important things in your business—while staying independent and resilient.  Success isn't final and failure isn't fatal. What matters is whether you keep going—and keep making progress. If you're still here, still building, still learning—you're doing something right. I respect practical founders who choose independence, solve real problems, and do hard things year after year. Key Takeaways Progress Over Growth Rates - What matters is whether you moved the hardest, most important parts of your business. Focus Is a Force Multiplier - Trying many things without concentration is why most initiatives stall. Companies Mirror Their Founders - The company's strengths and weaknesses often mirror the founder's. Cushion Creates Resilience - Cash, energy, and upsides protect businesses when headwinds inevitably appear. You Make It Up - How you frame last year's results shapes decisions, morale, and alignment. Quote from Greg Head, founder of Practical Founders "Everybody's doing really hard things who are practical startup founders. I know you are too. The question isn't about what the perfect growth rate or planning process is for you right now. The question is, are you lined up to actually do enough of the most important hard things in your business next year? Are you really set up to make the kind of progress you want along the bigger vision you have for the company? There are all kinds of ways to do it. You can go fast or slow, or it could be an invest year, a rebuild year, or a steady year. You can choose your growth rate, your profitability, and all of that.  "You get to do it your way. You've bought your independence, or you are paying for it the hard way. There's no one right way to do all of this, if you're making big progress and getting better every year in the eyes of your customers, employees, and the owners." Links Greg Head on LinkedIn Practical Founders on LinkedIn Practical Founder website Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ 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.

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 discusses how overexpansion, premature scaling, hiring missteps, and market-chasing derail both VC-backed and bootstrapped companies—along with the psychological patterns founders rarely acknowledge.  He shares lessons from his book "Reignition: Transforming Stuck Startups Into Breakout Winners" on why most stuck companies don't need a new strategy—they need a wiser founder who understands their inner operating system and is willing to grow alongside the business. Today Dave coaches founders, writes about the emotional foundations of leadership, and acquires underperforming SaaS companies to "refound" them with more clarity, connection, and human-first strategy. Key Takeaways Founder Psychology Matters — Most stuck companies trace back to subconscious patterns, not strategy failures, and founders must address these to grow. Premature Scaling Kills — Expanding markets or teams too quickly dilutes the core and creates complexity most companies cannot absorb. Core Before Expansion — Winning in a beachhead and protecting the core creates more durable growth than chasing adjacent market too early. Better Growth Pace — Sustainable companies grow at the pace the market allows; forced hypergrowth often destabilizes otherwise healthy businesses. Quote from Dave Hersh, Co-founder and Former CEO of Jive Software "I realized that 90% of stuck companies and failed companies are not the reasons that we say they failed. Like they didn't have product market fit or they ran out of cash or the founders didn't get along. It's the psychology underneath. If you actually look at the source of those problems, It was these very consistent psychological patterns that founders run into. "So hero complex, warrior, imposter syndrome, over identification with the company. It was all of these things that I kept seeing over and over again that led to the decisions that got them stuck. And so, yes, while it's true, they got out competed. Why did they go after the big market? What led them to do that? Why did they try to compete against these companies they were competing against? "And then you start to tap into what's really going on and you see: They're trying to earn validation. They are trying to get redeemed as an entrepreneur. They're trying to live up to their parents, their older sibling, their peer group. And it was that desire that led to them trying to go after this big market and raising too much money that got them stuck. And so I like to work with the source material, which is, Why did you do that?" Links Dave Hersh on LinkedIn Book by Dave Hersh: Reignition: Transforming Stuck Startups into Breakout Winners Dave Hersh website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. 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.

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 the years, the product expanded too broadly, creating UX and complexity challenges that later required a deliberate refocusing on core use cases.  Today, Referral Rock is profitable, founder-owned, and steady at its current revenue plateau as Josh rethinks pricing, packaging, product simplicity, and ICP focus. He shares practical lessons on avoiding over-complexity, hiring from what you've already figured out, returning to first principles, and treating plateaus as puzzles to solve rather than signs of failure. Key Takeaways Charge Early, Not Late – His first startup delayed monetization; Referral Rock asked for payment within days of launching an MVP. Pricing For Segments– Good-better-best failed for SMBs with wildly different referral economics; switching to two specific lanes solved misalignment. Do the Job First – Hiring worked only after Josh personally figured out support, sales, or marketing enough to define the role clearly. Plateaus Aren't Failure – Post-COVID shifts and SEO changes slowed growth, but Josh treats plateaus as system puzzles, not existential threats. Profit Equals Freedom – With no investors and steady profitability, he optimizes for enjoyable work, long-term optionality, and building at his own pace. Quote from Josh Ho, Founder and CEO of Referral Rock "For me, a plateau or a pivot is a puzzle to be solved. Any time you try to build something, you hope to just keep hitting accelerators and different serendipitously find those things. But I've learned through my life, the most part, there are things that work only for a certain duration, right.  "For me, it comes back to how I think about the business and. my innate goals for the business which, are different from most founders. When I'm talking to another founder is, they'll ask me what my exit strategy is. And my answer is usually, Well, I don't really have one. That's not how I think about the business. It's a very clear. "I enjoy my work and that's my North Star. Am I having fun? Do I enjoy this work? And I also continuously reinvent myself and my role to fit those changes.. There might be a job I had to do that I don't enjoy, but then I'll do that until it's no longer like the limiting step and then hire someone to backfill for myself." Links Josh Ho on LinkedIn Referra lRock on LinkedIn Referral Rock website Podcast Sponsor – Designli 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. 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.

Shailesh Hegde is the CEO of Hubilo, 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 marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing. Hubilo stabilized revenue, rebuilt its GTM motion, and reached a 50/50 split between new webinar revenue and legacy customers.  Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product. About 80% of Hubilo's team moved over, and Shailesh now leads product integration and customer continuity during the transition. He shares hard lessons on pivots, returning capital, leading through uncertainty, and executing a practical exit when the original VC-scale vision is no longer realistic.  Key Takeaways Refounder Mindset – Shailesh stepped into the CEO role and reframed the mission from hypergrowth to survival, focus, and a practical exit. New ICP Reality – Moving from event organizers to B2B marketers required a complete repositioning and GTM rebuild that took longer than expected. AI as Differentiator – Hubilo used AI-generated content and repurposing tools to stand out in a crowded webinar category with entrenched incumbents. Practical GTM – LinkedIn thought leadership, SEO content, and product-led demos outperformed outbound or expensive Google ads in this competitive space. Strategic Fit Wins – BrandLive acquired Hubilo for complementary capabilities, product acceleration, and access to a strong India-based engineering team. Quote from Shailesh Hegde, CEO of Hubilo "Now that I just sold our company, I'm thinking about what's next for me. It comes down to, Will I be able to find a viable problem that people are willing to pay for and will I be able to use sort of all of this experience that I have in order to solve it really well and kick off a company off the ground?  "Now is probably the best time to start a company where there's so much action, there's so much happening in AI, and it's super exciting to be in this space. It's also a great time to not have like revenue pressure on your shoulders and just think out loud, have open conversations and just be free, before you really dive in and choose a focus. "The same types of business pressures will come back as you start a company. But now is a great time to just help with transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup." Links Shailesh Hegde on LinkedIn Hubilo on LinkedIn Hubilo website Brandlive website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. 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.