30+ year software veteran, now hosts Practical Founders CEO peer groups and a weekly podcast for SaaS AI founders building their way without big outside funding

Southlake, Texas
Joined June 2008
Greg Head retweeted
📢 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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Greg Head retweeted
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 – at Austin, TX
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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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"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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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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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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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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Esben Friis-Jensen is the co-founder and CEO of Userflow, a no-code onboarding software. @esbenfj @getuserflow #PLG With $3 million in ARR, 600 customers, and 3 employees, Userflow is a profitable and growing business with no outside funding. practicalfounders.com/podcas…
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Growing a #Startup within a larger org: key ingredients for success? (1) Clarity of the #JTBD (2) Strong internal feedback loop (3) Resource separation (4) Financial support Talked about this with @GregHead on the Practical Founders podcast: practicalfounders.com/podcas…
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Greg Head retweeted
Always fun to meet up with @RebeccaClyde and @GreggScoresby to talk about tech start ups, and the challenges (and fun) that come with them, the phx ecosystem, and “slaying dragons” (shoutout to @GregHead for teaching me that one)
Replying to @azcommerce
Venture Madness Chair Hamid Shoajee and previous Venture Madness winners Rebecca Clyde, Will Shaw, and Gregg Scoresby sharing their journey from startups to investors. #VM23 @venturemadness and @botcoai, @betteragency, @greggscoresby, @phxventures.
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Replying to @Frances_Coppola
I’ve never been so glad to have bootstrapped our company and never taken funding. I think there is a growing movement for this (@GregHead )
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Replying to @GregHead
@GregHead had me unplugged and pulled out Lumel's history, vision, and DNA for everyone to listen to. lnkd.in/gknGGw5h
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Greg Head retweeted
👋Charleston 📣Listen to local business leader, @iamBradRedding talking about Elevar. We're a bootstrapped SaaS company, growing steadily with 45 remote employees. #2 on the 2022 Inc. 5000 list for #Charleston! player.fm/series/practical-f… @GregHead #Shopify @ChasCityPaper
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Grateful for the opportunity to tell some of my story as a first-time founder, owner, operator, investor, and inventor at @SquadCastFM. Thank you for creating on this amazing interview @GregHead! 🎧 practicalfounders.com/podcas…
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Greg Head retweeted
Republicans don't want to solve inflation by lowering costs. They want to solve it by raising taxes and lowering your income.
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In the game? It’s a tough, hard, stressful game. There are options for how you grow and build your business. This conversation with @GregHead was awesome. If you are a founder, a business leader, someone who is thinking about funding sources and options…lnkd.in/geHK2YxK
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Greg Head retweeted
Replying to @GregHead
It’s really is what adds an extra level of fun and belief in each other
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