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Practical Founders Podcast

Practical Founders Podcast

著者： Greg Head
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 Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.2025 Scaling Point LLC マネジメント・リーダーシップ リーダーシップ 経済学
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  • #175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh

    #175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh
    2025/12/19
    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 LinkedInBook by Dave Hersh: Reignition: Transforming Stuck Startups into Breakout WinnersDave 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.
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    1 時間 7 分
  • #174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho

    #174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho
    2025/12/12
    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 LinkedInReferra lRock on LinkedInReferral 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.
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    1 時間 7 分
  • #173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde

    #173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde
    2025/12/05
    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 LinkedInHubilo on LinkedInHubilo websiteBrandlive 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.
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    1 時間 9 分
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