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How Going Against Every Rule Built a Thriving Software Company with Alex Sanfilippo
Every mentor he paid told him to stop talking to his own software customers.
So he listened. Built a 17-person team. Removed himself completely.
And watched his company go numb.
On this episode of Black Sheep Network, I sit down with Alex Sanfilippo, the founder of Podmatch, and we get into one of my favorite Black Sheep truths: the advice that feels wrong for you IS wrong for you, no matter who's giving it.
Alex built Podmatch from a $5,000 bootstrap into a platform facilitating hundreds of podcast bookings a day. But the path there wasn't the shiny, scale-fast, delegate-everything playbook his mentors prescribed.
It was the exact opposite.
We talk about what happened when he followed conventional wisdom. Hiring 17 people. Removing himself from the front lines.
Growth stalled at $30K a month.
Then came the gut-punch moment at PodFest Orlando that changed everything. He met his most loyal user and didn't even know who they were.
Here's what we dig into:
This is not a story about being anti-advice. It’s about no longer abandoning yourself and creating your own blueprint instead.
If you've ever sat in a room full of people more successful than you and felt something in your gut screaming "this isn't right," this episode will feel like a deep exhale.
Go listen. Then go see what Alex built, because the way he runs Podmatch is proof that the Black Sheep way isn't just more fulfilling. It's more profitable.
ABOUT THE GUEST
Alex Sanfilippo is the founder of Podmatch, a platform that connects podcast hosts and guests for interviews without the chaos.
He bootstrapped it with $5,000. Grew it into a platform powering hundreds of daily bookings. Runs it with three people.
He's also the host of Podcasting Made Simple and the creator of the Pod Value Initiative, where Podmatch gives half its profit back to the podcasters who use the platform.
Former aerospace guy. Current podcasting advocate. Perpetual Black Sheep who got kicked out of a mastermind for refusing to stop caring about his users.
Find him at podmatch.com/free.
[00:04:45] 100+ podcasters lined up to tell him what they were struggling with
[00:06:00] $5,000, a whiteboard wall, and a co-founder from his wedding party
[00:07:00] "I felt like David in a room full of Goliaths"
[00:08:30] The mastermind advice that felt wrong from day one
[00:10:45] Standing in front of his biggest fan and not recognizing him
[00:12:00] Phasing out 17 people and getting removed from the mastermind
[00:13:15] $30K to $60K a month after one shift: being himself again
[00:18:15] Splitting profit in half to pay podcasters through the Pod Value Initiative
[00:21:00] "You're making us look bad." The backlash from other founders
[00:22:30] 80 bookings a day jumping to nearly 200
[00:24:00] Why people over profit always wins, and the data to prove it
[00:25:00] "We're letting our giftedness take us further than our character can"
[00:27:00] Where to find Alex and his no-strings-attached free resource
#BlackSheepNetwork #AlexSanfilippo #Podmatch #PodcastingMadeSimple #PeopleOverProfit #TrustYourGut #BootstrappedStartup #PodcastGrowth #EntrepreneurMindset #AntiHustle #FounderStory #PodcastCommunity #DoItDifferently #SmallTeamBigImpact #PodValueInitiative #AuthenticLeadership #PatternBreaker #BlackSheepManifesto
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By blacksheepnetworkEvery mentor he paid told him to stop talking to his own software customers.
So he listened. Built a 17-person team. Removed himself completely.
And watched his company go numb.
On this episode of Black Sheep Network, I sit down with Alex Sanfilippo, the founder of Podmatch, and we get into one of my favorite Black Sheep truths: the advice that feels wrong for you IS wrong for you, no matter who's giving it.
Alex built Podmatch from a $5,000 bootstrap into a platform facilitating hundreds of podcast bookings a day. But the path there wasn't the shiny, scale-fast, delegate-everything playbook his mentors prescribed.
It was the exact opposite.
We talk about what happened when he followed conventional wisdom. Hiring 17 people. Removing himself from the front lines.
Growth stalled at $30K a month.
Then came the gut-punch moment at PodFest Orlando that changed everything. He met his most loyal user and didn't even know who they were.
Here's what we dig into:
This is not a story about being anti-advice. It’s about no longer abandoning yourself and creating your own blueprint instead.
If you've ever sat in a room full of people more successful than you and felt something in your gut screaming "this isn't right," this episode will feel like a deep exhale.
Go listen. Then go see what Alex built, because the way he runs Podmatch is proof that the Black Sheep way isn't just more fulfilling. It's more profitable.
ABOUT THE GUEST
Alex Sanfilippo is the founder of Podmatch, a platform that connects podcast hosts and guests for interviews without the chaos.
He bootstrapped it with $5,000. Grew it into a platform powering hundreds of daily bookings. Runs it with three people.
He's also the host of Podcasting Made Simple and the creator of the Pod Value Initiative, where Podmatch gives half its profit back to the podcasters who use the platform.
Former aerospace guy. Current podcasting advocate. Perpetual Black Sheep who got kicked out of a mastermind for refusing to stop caring about his users.
Find him at podmatch.com/free.
[00:04:45] 100+ podcasters lined up to tell him what they were struggling with
[00:06:00] $5,000, a whiteboard wall, and a co-founder from his wedding party
[00:07:00] "I felt like David in a room full of Goliaths"
[00:08:30] The mastermind advice that felt wrong from day one
[00:10:45] Standing in front of his biggest fan and not recognizing him
[00:12:00] Phasing out 17 people and getting removed from the mastermind
[00:13:15] $30K to $60K a month after one shift: being himself again
[00:18:15] Splitting profit in half to pay podcasters through the Pod Value Initiative
[00:21:00] "You're making us look bad." The backlash from other founders
[00:22:30] 80 bookings a day jumping to nearly 200
[00:24:00] Why people over profit always wins, and the data to prove it
[00:25:00] "We're letting our giftedness take us further than our character can"
[00:27:00] Where to find Alex and his no-strings-attached free resource
#BlackSheepNetwork #AlexSanfilippo #Podmatch #PodcastingMadeSimple #PeopleOverProfit #TrustYourGut #BootstrappedStartup #PodcastGrowth #EntrepreneurMindset #AntiHustle #FounderStory #PodcastCommunity #DoItDifferently #SmallTeamBigImpact #PodValueInitiative #AuthenticLeadership #PatternBreaker #BlackSheepManifesto