Paid advisor to 40 practical SaaS founders building valuable software companies without big funding. Host of Practical Founders Podcast.

Joined June 2008
135 Photos and videos
Greg Head retweeted
9 Apr 2025
📢 What separates category leaders from the rest in vertical SaaS? Our founder, @davelyuan, recently joined @GregHead on the Practical Founders podcast to discuss the frameworks that help vertical SaaS companies win and scale––starting with control points. Why do control points matter? The control point is the last tool to be thrown out before an owner ceases operations, and more importantly, owning the control point gives you the unfair right to offer most products a merchant needs. When you own the control point, you become the multi-product platform for your vertical. Listen to the full conversation here: practicalfounders.com/articl…
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26 Mar 2025
A new wave of AI-powered features and products is bringing back the word “magical” to SaaS software, not just in the marketing hype. This has happened with every new wave of tech since the beginning of PCs and Macs.
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6 Aug 2024
Magical thinking about spending big to hire senior executives quickly is one of the main reasons SaaS founders raise large VC funding (and spend it on executive recruiters). But the "Hire Fast to Grow Big" approach usually doesn't work, so it creates more VC-funded SaaS companies that stall out and get stuck.
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31 Jul 2024
30% average annual revenue growth is healthy and sustainable for most bootstrapped SaaS businesses, but it's a nightmare if you raised big VC funding.
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29 Jul 2024
It’s not common for VC-funded software companies to acquire companies for partial cash plus equity, but it happens. VC-funded companies are much riskier than bootstrapped ones. SaaS founder interview with Ian Manners of Vivor. practicalfounders.com/podcas…
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Greg Head retweeted
14 May 2024
Today in Austin, Texas, our incredible co-founder & Chief Brand Officer, Rebecca Shostak, spoke at @SaaStock alongside @GregHead from Practical Founders about Flodesk's journey from launch to bootstrapping a startup to $23M in annual recurring revenue. During their fireside chat, Rebecca shared insights into her design philosophy and highlighted our deep-rooted commitment to empowering creators and small business owners. We're so proud. #Flodesk #SaasStock #StartupJourney
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19 Apr 2024
Serious SaaS founders have learned that pursuing big VC funding too early decreases their odds of success. The longer you can go without raising outside funding, the better your odds of success as a SaaS founder. Thanks, @finnthormeier, for the clip from your pod!
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Greg Head retweeted
Turns out, the best therapist for startup struggles is another founder who gets it! Tune in as @mattwatsonkc and @GregHead weigh in on the importance of in-person events for building strong relationships and solving real problems. startuphustle.xyz/saasopen-r…
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Greg Head retweeted
"The more money you raise and the bigger your investors, the lower your odds of succeeding." @GregHead Great e-Book from Greg on how to "Win the Startup Game Without VC Funding" (and, ideally bootstrapping) You can download it here practicalfounders.com/
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Greg Head retweeted
Yup. That’s my story. One VC told me I was “stupid” and that I would “ruin my career” pursuing innovation Games/Conteneo. @GregHead has a brilliant podcast series that focuses on practical founders - and our bank accounts are often much bigger than VC-backed founders when all is said and exited.
I have interview 3 $BN founders over the last week that raised no venture money and bootstrapped. I asked them; why bootstrap over the venture model? All three responded: We tried, every investor said no. No one believed. We had no choice.
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11 Oct 2023
I'm headed to Dublin next week to help out at the #SaaStock conference and meet practical SaaS founders from all over the world. See you there.
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22 Sep 2023
I just canceled my subscription to the @WSJ after being a paid subscriber for over 20 years. The new WSJ apps completely ruined the reading experience on both iPad and iPhone. Now it's just painful to use. WTF WSJ? They just pissed off all their long-time digital subscribers.
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Greg Head retweeted
Boast.ai bootstrapped their growth to $10 million ARR before taking an investment that allowed cofounder @lloyedlobo to have a life-changing payout. Lloyed shares his struggles to find balance for the first time after his startup adventure. practicalfounders.com/podcas…
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Greg Head retweeted
Practical founders can choose to create a great business AND a great life at the same time. It requires a deliberate and disciplined approach. @jordanfleming is doing it right now. He tells his story on the Practical Founders Podcast this week. practicalfounders.com/podcas…
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12 Jun 2023
Expert interview with a practical investor explains how growth equity funding can be a great fit for bootstrapped SaaS founders who want to keep growing but take some money off the table now.
Expert interview with Deepak Sindwani, B2B SaaS growth equity investor at @WavecrestGrowth Partners explaining what growth equity funding is and why it's different than traditional VC or PE, answers FAQs with no selling. #practicalfounders practicalfounders.com/podcas…
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30 May 2023
Want to know what's happening in valuations right now for SaaS exits of less than $50M? I dig in with @chriskern to hear what he sees in the M&A market for practical SaaS founders.
I interviewed Chris Kern on the Practical Founders Podcast to hear what he sees in the busy acquisition market for smaller SaaS companies. Chris thinks there are 100X more exits under $50M exits than those billion $ exits. @ChrisKern #practicalfounders practicalfounders.com/podcas…
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22 May 2023
Congrats to my friend Joshua Strebel on an amazing journey with @Pagely and doing it his own way for 15 years before the acquisition by GoDaddy. @strebel Thanks for sharing your story on the Practical Founders Podcast, Joshua. Arizona FTW. @practicalfoundr
Joshua and Sally Strebel intentionally built a valuable bootstrapped software company AND built a life with their families and interests at the same time. They had a life-changing exit too, only their lives didn't change much. @strebel @Pagely practicalfounders.com/podcas…
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