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Andrew Dudum
Co-Founder, Chairman & Chief Executive Officer, HIMS & HERS HEALTH INC

Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers

📅 Mar 10, 2026 BoomPop 51 MIN 4340 VIEWS 194 SEGMENTS · 2 SPEAKERS
Andrew Dudum built Hims & Hers from zero into a multi-billion-dollar consumer publicly-traded consumer health company by doing something most founders avoid: leaning directly into discomfort. He’s able to lead the hard conversations that most leaders avoid. In this episode, Andrew and I talk candidly about what it actually takes to scale a company and stay grounded while doing it. We unpack the lessons he learned by understanding mortality early, the emotional whiplash of running a public company, and why “being nice” is often the least kind thing a leader can do. Andrew shares the moment at...

Questions asked in this interview

11
  1. 3:00How did that start this whole thing?
  2. 4:28[laughter] And the hair products, right?
  3. 16:26So, like if you have two options, a good and a bad, you actually feel psychologically worse not knowing which it is versus just knowing it's the bad, right?
  4. 17:55It's like what's the long-term thing?
  5. 19:05You know, have I ever told you a story about Ryan Sarver and Jules Maltz?
  6. 22:59I remember this one time we were, we got like was it ice cream or donuts something in your neighborhood?
  7. 24:18And yet like you lead one of the fastest growing health companies in the world and so like how did you stay open to learning without pretending to have all the answers?
  8. 28:58Like what's your thoughts around that?
  9. 37:22How do you find the resilience to make it through some of that stuff?
  10. 41:36... someone listening to this and you're an early founder and you're kind of in the scale stage like any stories about when you got a specific piece of human feedback and it actually changed trajectory for how you were thinking about stuff?
  11. 47:26... self or to any emerging founder leader about a lot of these like very human-centric lessons you've learned over time what do you think it'd be like what would you want them to like really hear and understand earlier on in their careers?
Andrew Dudum 0:00 ↗
There's a superpower that I don't think people really appreciate, which is being comfortable being uncomfortable. That comfort being uncomfortable gets you through tough conversations. It gets you through pivots in the company. It gets you through days when the stock is down 15%.
Interviewer 0:15 ↗
Meet Andrew Dudum, CEO of Hims and Hers.
Andrew Dudum 0:19 ↗
When you go through in life, it was never more clear based on who showed up.
Interviewer 0:24 ↗
Yes.
Andrew Dudum 0:24 ↗
And a lot of people didn't show up.
Interviewer 0:26 ↗
Wow. A lot of people you interact with just don't show up because it's hard. It's uncomfortable.
Andrew Dudum 0:30 ↗
You know, when I was 12, my dad told me, we were sitting like in our living room and he looked at me and I'll never forget this, and he said, 'I'm dying. Everybody's dying. Just so you know, everyone's going to die. Like, you're the oldest son. You're the man of the house. Take care of your mom.'
Interviewer 0:48 ↗
Oh, God. 12.
Andrew Dudum 0:53 ↗
The difference between niceness and kindness. It's nice to not tell someone the hard thing because it's easier. They don't feel bad. But it's kinder to have the hard conversation that makes them fundamentally better as a human.
When my sisters were dating people, I would joke with my brother like if the first thing they say when they come back from the date is like, 'He's like such a nice guy.' I'm like, 'This guy has no chance.'
Interviewer 1:20 ↗
So Andrew Dudum isn't your typical tech CEO. He's built a multi-billion dollar healthcare company. And I'm very biased, but reputation as one of the most genuinely good guys in the business. And the twist is your success, Andrew, comes from kindness. Not the fake conflict-avoiding niceness, but real kindness that often means having tough conversations and doing the right thing even maybe especially when it's hard. And I remember we met, I think it was right after you dropped out of college.
Andrew Dudum 1:51 ↗
Yep. We were in the same fraternity but never actually overlapped. And I remember...
Interviewer 1:54 ↗
Thank God. Thank God for that. Yeah.
Andrew Dudum 1:56 ↗
The house would have burned down.
Interviewer 1:57 ↗
Yeah. Would have been bad.
Andrew Dudum 1:59 ↗
And remember like you were just coming to the Bay Area and it was like you, Dylan, Dan, a bunch of us. We'd like go sailing and stuff and we became friends. You obviously joined at Atomic. I then joined later. We kind of overlapped for a little bit and you've just gone on to do incredible things, man.
Interviewer 2:14 ↗
And obviously like I love the [ __ ] out of you. So thank you for doing this. I know you don't do this.
Andrew Dudum 2:19 ↗
I'm super happy to be here. This is a lot of fun.
Interviewer 2:21 ↗
I appreciate it, man. So, can we, I'm going to kick it off. Look, your company, Hims and Hers, is built upon having conversations people normally kind of avoid, you know, it's like sensitive stuff like, oh, you're losing your hair, you're having ED issues. There's all these things you do that are so important. And I think there's a part of this that may have started pretty young in your life about having tough conversations. And there's, you know, if you're willing to share it, there is this moment that we've talked about privately as friends where you were 12. Your dad was, I think, like 38.
Andrew Dudum 2:57 ↗
Mhm.
Interviewer 2:58 ↗
Yeah. He was my age.
Andrew Dudum 2:58 ↗
He was your age. Yeah.
Interviewer 3:00 ↗
And you got some really hard news about that. And that's got to be like a pretty crushing thing for a kid to go through. I'm just kind of curious like there's this spectrum of CEOs out there. Some are you call mercenary CEOs who kind of just do it for the money and some are missionary CEOs. And I feel like this is so deep for you. How did that start this whole thing?
Andrew Dudum 3:20 ↗
You know, when I was 12, my dad told me we were sitting like at our living room couch and my mom was there, my grandparents were there, and he looked at me and I'll never forget this, and he said he's like, 'I'm dying. Everybody's dying. Just so you know, everyone's going to die.' Andrew, he's saying this to me when I'm 12. I just might know what kills me, right? I might just be aware of it. That's how he said it.
Interviewer 3:47 ↗
That's how he said it. Wow.
Andrew Dudum 3:48 ↗
And then, you know, I don't remember a lot of it because I feel like your body naturally just kind of blocks out different dynamics of that. I also remember the night before he went into surgery, it was stage four colon cancer, which by the way, for the average person, you do not get stage four colon cancer at 38, right? That is not heard of. The actual testing doesn't begin until 50 for the average male. So, we'll come back to that because I think it really ties to a lot of the stuff we're doing with Hims and Hers today and a lot of the mission, but it was a diagnosis that was shocking, right? And I think about it a lot because I am now that age and I have three little...
Interviewer 4:28 ↗
Thank you. I moisturize with Hims. [laughter] And the hair products, right?
Andrew Dudum 4:32 ↗
So I'm the same age as my dad when he was diagnosed with stage four cancer. I have three little babies. He had four little babies.
Interviewer 4:38 ↗
Yeah.
Andrew Dudum 4:39 ↗
And the idea of the fear of that as a father today really shakes me. But I remember being 12 and being taught that data was not scary.
Interviewer 4:54 ↗
Oh, interesting.
Andrew Dudum 4:55 ↗
Learning things was not scary. What was scary was not knowing. And my dad self-diagnosed himself with stage four cancer. He spent like, this is early internet days. It was like WebMD type channels and discussion boards where he was piecing together his symptoms. The doctors, he brought it to them. They said no.
Interviewer 5:18 ↗
They declined the testing because you just don't get cancer at 38 of stage 4.
Andrew Dudum 5:22 ↗
It turns out it's a very specific genetic predisposition that nowadays you can get testing for and it's easy to recognize. But we were taught really early that information is not scary.
Interviewer 5:33 ↗
Yeah, information is a blessing that you can then do something about.
Andrew Dudum 5:37 ↗
Totally. And I think from an early age being taught to confront the reality of mortality at a very young age gives you a conversation about perspective of life, right? Because you don't think about that usually until I don't know 30s or 40s when your parents are sick. I thought about it when I was really early. And then also a conversation about responsibility. So, the night before my dad went into surgery, he gave me, he had, he doesn't have it anymore, a pendant that was kind of like this one. It was a Mother Mary pendant, kind of a Catholic pendant that he always wore as a kid. And I just remember like playing with it. And he always had it on. And he took it off and he gave it to me.
Interviewer 6:22 ↗
Oh.
Andrew Dudum 6:23 ↗
And he's like, 'This is yours. You're the oldest son. You're the man of the house. Take care of your mom. Take care of the kids.' Like we're first, second generation Palestinian so it's like kind of old school type talk right? It's not modern-day parenting like this is a kind of immigrant conversation. But there was that heaviness and clarity of like you have a set of responsibilities that is unique.
Interviewer 6:50 ↗
Holy [ __ ] your dad literally the pendant he had worn his whole life he handed to you the signal being...
Andrew Dudum 6:56 ↗
This, you might be wearing this now. Yeah, exactly. God. Yeah, I gave it back to him. Which is great. But that sense of responsibility and information is really interesting.
Interviewer 7:21 ↗
It is. And we live today in a world where that information for most people you just can't get access to.
Andrew Dudum 7:28 ↗
Yeah. Right. Like I'll give you an example. My father-in-law has had multiple heart attacks. Then he had a heart attack at age 50 and then another one I think like 10 years later. And in both situations he was pronounced dead. They like froze his body and they resuscitated him, unfroze him and brought him back to life. It was like severe life-ending attacks.
Interviewer 7:54 ↗
But and remind me, he's a data guy. He's like a physicist.
Andrew Dudum 7:56 ↗
He's a physicist. He's like a famous physicist. He rides his bike 40, 50 miles a weekend. Like I can't keep up with this guy. And just like heart attack.
Interviewer 8:04 ↗
Holy.
Andrew Dudum 8:04 ↗
And in both situations, my wife and my mother-in-law told me that he went to the cardiologist like a week or two before and the cardiologist was like, 'Hey, your cholesterol numbers are looking great. You're like, keep it up. You're doing a great job. Keep it up.' And then boom, two weeks later.
Interviewer 8:19 ↗
Oh my god.
Andrew Dudum 8:20 ↗
And it wasn't until a few months ago that I got him testing for some more advanced genetic predisposition markers.
Interviewer 8:29 ↗
Because you now know all this. And now I know this is like what you know.
Andrew Dudum 8:32 ↗
Yeah. This is what I do all day. And there's one test called lipoprotein little A. It's a genetic predisposition to heart attacks. And if you have an elevated lipoprotein little A and your cholesterol numbers are perfect, you're [ __ ].
Interviewer 8:46 ↗
What? Yeah, like you're going to have a heart attack.
Andrew Dudum 8:49 ↗
In order to be okay with an elevated lipoprotein little A, with this elevated risk factor, you need your cholesterol numbers to be spectacular. Like spectacular to a degree. Most doctors would be like, 'What are you like seven? Like this is crazy numbers.'
Interviewer 9:07 ↗
Wow.
Andrew Dudum 9:08 ↗
And there's medicines for this. There's statins, there's PSK9 inhibitors, there's injections, there's all types of stuff that you can do if you have this predisposition to reduce that risk.
Interviewer 9:18 ↗
Yeah.
Andrew Dudum 9:18 ↗
He found out at 65 after two heart attacks that he has this risk.
Interviewer 9:22 ↗
Oh my gosh.
Andrew Dudum 9:23 ↗
So, we then went through the process of testing everybody we knew. Seriously. Like everybody that we in our family that came from this lineage in mine, we tested and half of them have a number that's off the charts.
Interviewer 9:36 ↗
No way.
Andrew Dudum 9:37 ↗
Yeah. And we've got, you know, I've got siblings and cousins that are in their 40s who are incredibly healthy with perfect numbers and have no idea they're 10 years away from a genetic heart attack.
Interviewer 9:49 ↗
Oh my god.
Andrew Dudum 9:50 ↗
And so this idea of just like responsibility and access to information is something that is really important to me. And I think it shows up in, you know, why I still run this business. It's maybe like one of the only reasons I still run this business is just because I think that's so impactful. But that requires hard conversations because it's so [ __ ] uncomfortable to get that result. It's so uncomfortable to confront that reality and to piece it together. It's so much easier and I see my buddies do this all the time and a lot of our shared friends like, you know, 'I'm not going to, I'm fine, like I go for a run, not to know.'
Interviewer 10:31 ↗
Yeah. It's easier not to know things.
Andrew Dudum 10:33 ↗
And I have, you know, made it something that is a pillar of my life to push those conversations, to be comfortable in the uncomfortable for a better good, which is getting education out there.
Interviewer 10:47 ↗
What an amazing thing just to say this back to you for 5 seconds. You realized early on not just the power of data, but how the power of tough conversations, being comfortable in the uncomfortable, literally saves lives. And you started a whole company that just does that.
Andrew Dudum 11:02 ↗
It's a superpower. I've thought this for a long time.
Interviewer 11:05 ↗
That's amazing.
Andrew Dudum 11:06 ↗
There's a superpower that I don't think people really appreciate, which is being comfortable being uncomfortable.
Interviewer 11:14 ↗
Say more.
Andrew Dudum 11:15 ↗
Like it's a, I don't know. I think about this a lot. Like in order to have hard conversations, in order to confront tough things, in order to build teams and make changes and fire people, like running companies, like people ask me like what's a key trait and one of the ones I keep coming back to is just like so much of great execution I think is really, really hard and it's not like difficult like physically, it's like emotionally hard.
Interviewer 11:44 ↗
Yeah.
Andrew Dudum 11:47 ↗
And so getting your body and your mind comfortable being uncomfortable is I think like one of my superpowers, you know, and I think part of this also stems even just from my predisposition like I've probably told you this since I was a teenager. I've had panic attacks, right? So I like hate doing podcasts. Like I hate, I really appreciate you doing that, right? Like it's not my top fun thing to do. And I've gotten comfortable with like being on stage and being like, 'Oh, wow. Panic attacks hitting. [ __ ] That's really uncomfortable.' And then being like, 'All right, I got it. It's kind of going over.' You know, and so that comfort being uncomfortable gets you through tough conversations. It gets you through pivots in the company. It gets you through days when the stock is down 15%, 20%, whatever it is, right? You just recognize you're in this moment of time that is not perpetual, is going to change and in this moment this wave is uncomfortable and you are extremely well equipped to sit there in that uncomfortable period.
Interviewer 12:53 ↗
That's amazing. I want to talk about for a second the difference between niceness and kindness. I think it's actually like a really important concept for the idea of having hard conversations, being okay with feeling not okay. Like it is nice to smile at someone and actually it's nice to not tell someone the hard thing because it's easier. They're not going to feel bad.
Andrew Dudum 13:14 ↗
But it's kinder to have the hard conversation that makes them fundamentally better as a human, fundamentally safer as a patient, fundamentally more healthy. All those things are true. And I remember, you know, I was chatting with the amazing Sarah on your team and she was saying how you have many mantras and everyone should know this, like everyone who works on your team [ __ ] loves you. I mean that you don't hear that often actually. You really don't hear it and it's so deeply true. And she was saying that one of your mantras was if you want to have impact at this organization you have to have tough conversations.
Interviewer 13:50 ↗
It's interesting because in health I think specifically one of the biggest barriers as you mentioned and it's in leadership too, it's kind of like avoidance.
Andrew Dudum 13:57 ↗
Yeah.
Interviewer 13:58 ↗
And nearly two-thirds of men, I always look up these studies and stuff, nearly two-thirds of men say they delay going to the doctor as long as possible.
Andrew Dudum 14:05 ↗
Yeah.
Interviewer 14:06 ↗
Mostly because of weird reasons like embarrassment, fear of bad news or not wanting to seem weak or something. And like that avoidance, that silence, it comes at a tremendous cost. Tremendous cost. Which by the way, just to take it back to your dad for a second, what a badass.
Andrew Dudum 14:23 ↗
Yeah.
Interviewer 14:24 ↗
All these pros are like, 'Well, we don't know.' He's like, 'No, I'm going to figure this out.' And then despite, I mean, there's... And obviously I know your dad. He's like one of the best humans on the planet. So, I'm not surprised, but we've actually never talked about it to this detail. So, that's... Anyway, the niceness versus kindness is an interesting subject, though.
Andrew Dudum 14:43 ↗
Yeah. Like that. I don't think there's enough nuance in people's mind between the two.
Interviewer 14:48 ↗
I agree.
Andrew Dudum 14:49 ↗
And there's huge differences in my mind. My wife is from Minneapolis, right? You know, so like I hear about Minneapolis nice, like Minnesota nice all the time, right? It's like just smile. Like we're like, 'Hey, everything's good. Everything's good.' And it's total [ __ ]. It's just a fake smile, right? That's what that means.
Interviewer 15:04 ↗
Yes.
Andrew Dudum 15:04 ↗
And you know, when my sisters were dating people, I would joke with my brother like if the first thing they say when they come back from the date is like, 'He's like such a nice guy.' I am like this guy has no chance.
Interviewer 15:15 ↗
Like if nice is the first thing you say when you talk about a person...
Andrew Dudum 15:21 ↗
It's a placeholder.
Interviewer 15:22 ↗
Oh, interesting.
Andrew Dudum 15:22 ↗
Right. It's a placeholder for like they're a pleasant person. They didn't do anything wrong. They were just there. They smiled. They had some courtesy, right? All great things, right? All important things. But super different from kindness. Like super different.
Interviewer 15:39 ↗
And I agree. I don't think enough people realize that.
Andrew Dudum 15:41 ↗
Yeah. I think kindness is actually about respect. It's an emotional, intellectual respect for the other person and thoughtfulness for how I'm going to interact with you. That might be honesty, might be directness. There's I think like an underlying thoughtfulness, understanding and respect in communication that is at the core of kindness.
Interviewer 16:06 ↗
Totally.
Andrew Dudum 16:07 ↗
And often that means tough things like tough conversations, honesty, right? Like transparency. Still doing it with kindness, right? Like in the right way. But you still got to do it, right? Like nice doesn't do the thing. Nice is the smile.
Interviewer 16:23 ↗
That's right.
Andrew Dudum 16:24 ↗
Kindness does the thing.
Interviewer 16:26 ↗
I completely agree. There's actually a bunch of psychology studies that clearly point to humans in indecision. It is the worst mental state to be in. So, like if you have two options, a good and a bad, you actually feel psychologically worse not knowing which it is versus just knowing it's the bad, right? And one of the nice tactics I've seen is like, 'Oh, well, let's give it a little more time. Let's see how it goes.' That delaying, oh, it's actually unkind to the person as a result. And there's something about, you know, one of the things we say, and I probably learned this from my very Italian wife, Rachel, who, you know, conflict is love. [laughter] Italian is it's important to be conflict-seeking without being an [ __ ].

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APA

Dudum, A. (2026, March 10). Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers [Interview transcript]. BoomPop. CEOInterviews.AI. https://ceointerviews.ai/interview/758572/

MLA

Andrew Dudum. "Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers." BoomPop, 10 Mar. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/758572/.

BibTeX
@misc{dudum2026_758572,
  author       = {Andrew Dudum},
  title        = {Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims \& Hers},
  howpublished = {Interview transcript, BoomPop. CEOInterviews.AI},
  year         = {2026},
  month        = {mar},
  url          = {https://ceointerviews.ai/interview/758572/},
  note         = {Speaker-attributed transcript with timestamps}
}