Healey Cypher

Husband/Dad, 4X Founder, just trying to be a good person every day | CEO @BoomPopHQ • COO @JoinAtomic

[Healey Cypher @healeycypher]

@briannekimmel Easy to do when guests are as thoughtful and badass as you!

[Healey Cypher @healeycypher]

A friend told @pbakaus it was "criminal" that he was giving his work away for free.

Paul considered that a WIN. Here's the mindset behind it, from my full episode of DBAJ with Paul. Live everywhere. 💌

[Healey Cypher @healeycypher]

@pbakaus New episode with Paul Bakaus:

Spotify: https://t.co/Y22IKJ1ZWf

Apple: https://t.co/I8YIrEFfci

Youtube: https://t.co/4lKqs5AUxs

[Healey Cypher @healeycypher]

@pbakaus spent years figuring out what makes creators build REAL audiences. He did that at Google as their first Head of Creator Relations, then at Spotter building AI tools for MrBeast and Dude Perfect.

What he kept finding: the creators who built genuine fans understood something about the people watching them that most people building products, teams, and companies miss entirely.

New episode of Don't Be a Jerk with Paul. Here's some of what we cover:

- Why the best car salesman in history outperformed everyone by 10x using one postcard
- What a Pixar director taught Paul about the thing that never changes in storytelling
- Why Paul open-sourced his best work and when a friend called it "criminal," he took it as a compliment
- What happens to men who build their whole identity around work and then retire
- Why most people are getting mediocre results from AI, and what the people getting great results do differently

This episode of DBAJ with Paul is live everywhere now!!!

[Healey Cypher @healeycypher]

"I spend more time with Healey than I do with my wife."

He’s not lying… as co-founders, we do see each other more than our own wives (sorry Rach!).

That’s why you need to choose VERY carefully who your co-founder is because the majority of your time will be spent with them. I got lucky with mine 😉

New episode with @BlakeHudelson, co-founder at @BoomPopHQ, is live everywhere!!!

[Healey Cypher @healeycypher]

@fordsmith @BlakeHudelson 💯

[Healey Cypher @healeycypher]

65% of startups fail because co-founders can't get along. Well, we’re happy to consider ourselves in the 35% of those that do.

I never planned to interview my own co-founder on this show. But here we are!!!

Here's the backstory:

@BlakeHudelson and I met at Atomic, a startup studio in San Francisco. A mutual contact introduced us and something clicked. So I did what any totally reasonable person would do… I suggested we work on 3 *companies at the same time* to see what sticks.

Blake said yes. Which tells you everything about him.

That was six years and roughly a thousand late-night calls ago. We've been through near-death moments, leadership changes that hurt, a Covid basement where I may or may not have screamed into a wall, and more pivots than either of us likes to count. We finally landed on @BoomPopHQ's direction in 2023 and haven't looked back.

This episode gets real and raw on our co-founder dynamic and some lessons we’ve learned that hopefully you can apply to your own co-founder relationships (or really ANY relationship, professional or otherwise). Blake tells you exactly what drives him crazy about me (including a habit of mine he's named the "super poop"). I'll admit what I should have done differently. And we share the stuff we genuinely wish someone had told us in year one.

What we get into:

- The one exercise every co-founding pair should do in their first 30 days
- Why our most important pivotal moments have always come from our disagreements
- What we learned from hiding problems from our team (spoiler: don't)
- The difference between a co-founder who complements you vs. one who mirrors you
- How radical transparency became the most powerful thing we ever did for our culture

New episode of Don't Be a Jerk with my co-founder Blake Hudelson is live now everywhere you get your podcasts!!!

[Healey Cypher @healeycypher]

@BlakeHudelson Listen to the full episode here:

Spotify:https://t.co/zc3nw62Qnf
Apple: https://t.co/qwtGYGoS6d
Youtube: https://t.co/YaYZRYPx8T

[Healey Cypher @healeycypher]

There's a study by psychologists Tedeschi and Calhoun that I can't stop thinking about. 50-70% of people who face significant adversity report positive growth afterward. The growth isn't correlated with how severe the adversity was. It's correlated with how much a person had to rebuild their assumptions about what's possible.

The Buddhist framing of this is almost identical: the pursuit of life is joy, but growth comes through suffering.

I had this conversation with @danh_trang after getting off the phone with a friend who studies Buddhism seriously. We sat with the weird duality of it. You want a joyful life. You also know the hard moments are the ones that made you.

He talked about being a father to two daughters and how he thinks about this constantly: how do you protect your kids from unnecessary pain while also knowing that some challenges are exactly what makes them who they become?

He wouldn't be who he is if his parents had shielded him from hard things.

The best leaders I know have all done some version of this. They got there by going through the hard things and learning something nobody else was willing to learn.

[Healey Cypher @healeycypher]

@danh_trang's parents left Vietnam in the late 70s with nothing. They had a kid who looked completely different from them. And just figured it out.

That kid went on to run the Boston Marathon seven times, become one of the fastest short-statured people to do it, and is now a partner at @southpkcommons backing some of the most interesting early-stage founders out there.

This was one of my favorite conversations I've had on the show. Swipe through and give it a listen wherever you listen to your podcasts!

[Healey Cypher @healeycypher]

@danh_trang @southpkcommons Listen into the full episode here: https://t.co/ljNfeK3eSs

[Healey Cypher @healeycypher]

@danh_trang was standing near the finish line when the 2013 Boston Marathon bombs went off. He came back the next year and ran it. And he's now ran the Boston Marathon 7x (!!!)

My guest on DBAJ this week is Danh Trang, partner at @southpkcommons. They have invested in companies such as Gamma, Baseten, Render, and Profound. (And he’s also a dear old friend from our time at Penn!)

What makes this one of my favorite conversations on DBAJ: Danh has spent his entire career running toward the hard thing, not despite his circumstances but because of them. And it's shaped one of the most original approach to investing in people I've ever encountered.

What you'll learn in this episode:

- Why SPC watches founders for 9-12 months before funding them, and what you learn when someone can't perform anymore
- What Danh reads in body cues during a 60-minute pitch and why he trusts it less than 9 months of watching someone in the wild
- The Marshall Rosenberg four-step framework that changes how every hard conversation goes
- Why the #1 cause of startup failure isn't the product or the market timing

- How his parents, who came from Vietnam with nothing, shaped everything about how he leads and loves

Danh is one of the most grounded, warm, and extraordinary people I know. Full episode is live everywhere you get your podcasts!

[Marc Andreessen 🇺🇸 @pmarca]

When one thing becomes abundant and cheap, another thing becomes scarce and valuable.

[Healey Cypher @healeycypher]

The US has the highest percentage of incarcerated citizens of any country in the world. The recidivism rate hovers around 50-60%. And prison is an $80 billion industry that you and I are bankrolling.

@hillaryblout has spent her career trying to change that… first as a prosecutor, now as the founder of For the People. She joined me on ‘Don’t Be a Jerk’ this week to talk about how the system actually works, and what it’s going to take to fix it.

Full episode is live everywhere!

[Healey Cypher @healeycypher]

@hillaryblout https://t.co/Zcis680Rgn

[Healey Cypher @healeycypher]

This former prosecutor went from sending people to prison to then building the legal system to bring them home. In our newest episode of DBAJ, we talk all about why she made this 180º career pivot and what she’s doing to flip the narrative around prison sentences.

@hillaryblout left the DA's office and built an entirely new legal pathway to bring people home from prison. Not by fighting prosecutors but by making them partners.

Her nonprofit, For The People, has helped resentence over 1,000 people across six states. The recidivism rate is 3-8%. The savings in one county alone is up to $287 million.

This is one of the most powerful conversations I've had on Don't Be a Jerk. We get into:

- Why the person you think is your opponent might be your best collaborator
- How she convinced "tough on crime" prosecutors to revisit their own cases
- The trauma-to-prison pipeline for women (500% increase since the 1980s)
- Why second chances produce better outcomes than punishment, with the data to prove it
- What perspective-taking looks like in practice, for leaders in any field

[Healey Cypher @healeycypher]

Ever been to a dinner party and feel like the other person will NOT STOP TALKING??? Yeah, me too…

My wife and I have a game we play at dinner parties. The goal is to ask as many questions as possible, and talk about ourselves as little as we can. It sounds simple, but it's surprisingly hard. And it has completely changed how we feel after almost every social situation.

Here's the science behind it: Harvard researchers found that talking about ourselves activates the brain's reward centers, the same regions fired by food or money. We are biologically wired to love it.

Which means that when you dominate a conversation with your stories, your accomplishments, your opinions, you're accidentally denying the other person something their brain is craving.

And they feel it, even if they can't actually say it.

Real listening is rare.

Most people are waiting for their turn to talk, mentally rehearsing their next point while someone else is still mid-sentence. To actually listen, to give someone your full, undivided attention, is one of the most uncommon things you can offer another person. And it's one of the most powerful.

The people who are genuinely fun and exciting to be around have figured this out. They ask more than they tell. They're curious more than they're clever. And they make it their goal to listen, not just hear.

They leave every conversation making the other person feel like the most interesting one in the room.

[Healey Cypher @healeycypher]

A simple trick that changes how people feel about you: Ask way more questions than you answer.

The most likable people aren't the loudest ones in the room. They're the ones who make you feel heard. And according to Harvard research, people genuinely enjoy conversations more when they do most of the talking.

So the next time you're in a meeting, on a date, or at a dinner party, make it a game. How many questions can you ask? How little can you talk about yourself?

You might be surprised how fascinating people think YOU are when you barely say a word about yourself.

[Healey Cypher @healeycypher]

https://t.co/IcExxzh8C2

[Healey Cypher @healeycypher]

I've been obsessed with this question lately: how does someone FEEL in the moments after they interact with me?

As Maya Angelou famously said:

“At the end of the day people won't remember what you said or did, they will remember how you made them feel.”

It turns out this answer matters more than most of us realize. When people feel respected, trust skyrockets. When they feel dismissed, defensiveness kicks in almost instantly.

So I did a solo episode on exactly this. 7 things you can do to be a genuinely great person. 5 traps that make you look like a jerk, even when that's not your intent.

What you'll walk away with:

- Why praising in public and giving feedback in private changes everything
- The "three times" name trick that makes people feel instantly seen
- Why the most likable people in any room talk the least about themselves
- What happens neurologically when you smile at someone (it's a little wild)
- How to change someone's mind without ever making an argument

This is one I'm really proud of.