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Index/Product/Fireside Product Management
Fireside Product Management artwork

From Band Drummer to BizDev to XFN Leader

Fireside Product Management · 2026-01-19 · 1h 11m

0:00--:--

Key moments - from our scoring

Substance score

45 / 100

Five dimensions, 20 points each

Insight Density8 / 20
Originality8 / 20
Guest Caliber11 / 20
Specificity & Evidence11 / 20
Conversational Craft7 / 20

Amanda Krantz brings a uniquely interdisciplinary perspective to business development, having worked as a PM at AT&T, Launch/Yahoo, and AOL Mail before pivoting to BD roles at startups and most recently joining Calagon as a cross-functional leader. Her AT&T story about ringtone cards illustrates the core tension in BD: the difference between signing deals customers ask for versus building the right product. When Walmart's buyer demanded a country music ringtone card, Krantz pushed back and ran experiments proving that hip hop (with its beat-heavy appeal) and branded content (like Simple Plan) outperformed genre-based selections. This parallels product management's core challenge - balancing customer requests with what actually drives behavior. At Calagon, Krantz applies this philosophy at a different scale, carefully evaluating partnership opportunities with Hyundai, motorcycle manufacturers, and Collins Aerospace against the company's current manufacturing capabilities (7-14 day custom turnarounds in high-margin, low-volume). She argues that BD and product management are inseparable in early-stage companies; the deals you don't sign matter as much as the ones you do. She also critiques how well-funded companies like Ramp lose sight of primary user needs by shipping too many features, illustrating how resource abundance can paradoxically degrade product focus.

Key takeaways

  • →BD and product management are deeply intertwined at early-stage companies because the deals you pursue directly determine your engineering roadmap and whether you're building the right product or just what customers ask for.
  • →Saying no to high-profile partnership logos (like Hyundai or major automotive deals) is often the right call if they misalign with your current manufacturing model, margins, and engineering capacity - opportunity cost and ongoing maintenance costs matter more than short-term wins.
  • →The best BD approach combines curiosity (asking 'why?' when told something can't be done) with experimentation; running tests at scale beats debating stakeholders until you're 'blue in the face' about what will actually sell.
  • →Well-funded companies often lose product focus by shipping too many features without maintaining excellence in primary use cases; Ramp's money-moving delays while adding features shows how feature velocity without strategic prioritization erodes trust.
  • →Early-career BD professionals are vulnerable to chasing deals because they want credit for landing logos, but experienced operators evaluate partnerships through a longer lens of whether they support or distract from core business momentum.

In this episode

  1. 1Amanda's Unconventional Career Path: From Air Force to Music to Startups
  2. 2The AT&T Ringtone Cards Project and Business Development Principles
  3. 3Balancing Deal-Making with Product Strategy at Calagon
  4. 4Understanding Business Development as Strategic, Not Transactional
  5. 5Lessons from CES: Major Companies Seeking Early-Stage Technology
  6. 6Product Focus and Feature Discipline: Learning from RAMP and Software Economics

Mentioned

Amanda KrantzAir Force AcademyLockheed MartiniTunesLaunchYahooAT&TAOL MailAmazon Prime AirGoogleCalagonCollins Aerospace

Guests

Amanda Krantz

Topics in this episode

Business development strategyProduct management alignmentAT&T prepaid music cardsRingtone market segmentationSimple Plan (band partnership)Walmart and Target retail partnershipsCalagon (wheelchair cushions and aerospace seating)Air Force B52 cushion SBIR contractsHyundai Palisade partnershipCollins Aerospace (commercial aviation seating)

Questions this episode answers

What's the difference between business development and sales?

Sales focuses on closing volume and growing fast; BD is about being slow and thoughtful, with equal emphasis on the deals you don't sign. BD requires strategic alignment with product roadmap and company capabilities, whereas sales is primarily about how much you can sign.

How do you decide whether to pursue a partnership opportunity when a major company approaches you?

Evaluate it against your current product, manufacturing model, and engineering capacity. Hyundai's high-volume, low-margin automotive business was incompatible with Calagon's 7-14 day custom wheelchair cushion model, so Krantz pursued Collins Aerospace instead - smaller volumes and closer alignment with their Air Force certification work.

Why did Amanda run an experiment with ringtone cards instead of just giving Walmart what they asked for?

She recognized that country music (what Walmart's buyer assumed would sell) didn't match the actual product - early ringtones relied on beats, not full songs, and hip hop dominated because of its beat-heavy appeal. The experiment with three variants (country, hip hop, and Simple Plan branded) proved hip hop and artist partnerships outperformed genre-based cards.

How does feature proliferation hurt product when you have unlimited resources?

Companies like Ramp that raise heavily often lose focus on primary use cases by shipping numerous features; when Ramp couldn't reliably move money from investment to business accounts at month-end while adding tangential features, it eroded user trust and threatened account migration.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

8 / 20

A handful of genuinely useful BD/PM insights (deals you don't sign matter more than deals you do; genre doesn't predict ringtone purchase, artist loyalty does; fix core functionality before layering features) are scattered across 71 minutes of career autobiography, drumming tangents, poker-with-kids anecdotes, and achievement-culture philosophising. The signal-to-noise ratio is low for a working operator.

BD I think is so much more important to be slow and thoughtful and it's the deals you don't sign
I actually took. In the spirit of, like, lifelong learning, I took an intro to drumming class a few weeks ago

Originality

8 / 20

The ringtone experiment framing (artist loyalty over genre) and the 'revenue exceeds capital raised' heuristic for real-business viability are mildly fresh; everything else - disagree-and-commit, lean in/out, don't build Christmas-tree products, be authentic - is well-worn PM and career-advice content.

people don't buy music based on the genre. They buy it based on a band that they like
if you have a series a startup that they have more revenue than dollars they've raised, they're a good candidate for actually having a real business

Guest Caliber

11 / 20

Amanda is a genuine multi-role practitioner (BD, PM, founder, finance) with real scar tissue across AT&T, AOL Mail, drone and healthcare startups, and current defence-adjacent manufacturing - but her roles have been at small scale and she is not a recognised operator who has built or scaled a large organisation; she is compelling as a journeywoman rather than a domain authority.

heading up business development, also having our product management group report to me, and running finance at a startup
I was a BD hire at an early stage company and then was a product manager for AOL Mail

Specificity & Evidence

11 / 20

Named entities are plentiful - Walmart Bentonville, Sony Music, Warner Music, Simple Plan, UCSF Benioff, Kaiser, Hyundai Palisade, Collins Aerospace, B52 SBIR - which anchors many anecdotes in real detail; however almost no hard numbers, timelines, or dollar figures are provided, limiting the evidence quality.

I got to go to Bentonville, Arkansas to meet with the music buyer at Walmart
we put our tech into a, uh, Hyundai Palisade and then went to Korea and demoed it, um, for their executives

Conversational Craft

7 / 20

The host is warm and occasionally surfaces a useful reframe (incentives driving PM shipping behaviour, fit-for-purpose hiring), but the conversation repeatedly collapses into mutual storytelling - drumming lessons, poker nights, Palo Alto parenting - with no substantive pushback or probing follow-ups on the BD or PM claims made.

Wow. Yeah. They. I do. I think you are pointing out like they raised a bunch of money.
That sounds amazing. I kind of feel like I want to add one to my Aeron chair

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B64%
  • Speaker A36%

Most-used words

product34didn30different25back24deal21school18music18startup17first15started14career14worked14point14trying13place13feel13

Episode notes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit firesidepm.substack.com

Full transcript

1h 11m

Transcribed and scored by The B2B Podcast Index.

Speaker A: All right team, we are back in the Fireside PM podcast and I have a classmate of mine from grad school, Amanda Krantz, in the, in the, in the episode today. Welcome to the show Amanda.

Speaker B: Thanks Tom. Good to be here.

Speaker A: Uh, where are you calling from? And just tell us a little bit about yourself for the audience so that they can get to know you and we'll dive deep into biz dev. I know that'll be a topic that we'll unpack a little bit but uh, give us a little bit of your background.

Speaker B: Sounds good. Um, so I'm calling from Bend Oregon. It's ah, up in central Oregon so more mountainy, kind of like Colorado versus the rainy Portland that people often think of. Um, moved here 10 years ago so pre way pre pandemic and been able to work remotely from here which has been awesome. Um, my background was ah, started out electrical engineering at the Air Force Academy and, and was in the Air Force for six years and had a pretty awesome career. I got to go to grad school in D.C. and then I worked out in Silicon Valley at Lockheed Martin Missiles in space during the dot com boom. But as a in plant acquisition person at Lockheed Martin and then went back and coached Division 1 college tennis at the Air Force Academy before going to business school. And then when I got out of business school I wanted to combine technology with business and music which was my passion and interviewed at itunes to be the first product manager there but didn't get the job and ended up at Launch which got acquired by Yahoo. So I got to kind of see music down in Santa Monica and a little bit of what a big company was like. Um, and then from there worked uh, at AT and T and was a business development product manager. So that was kind of began my kind of combo type role where you're doing innovation, where you're doing deals and product management kind of combined and we did prepaid ah, prepaid music content cards. So it was the era of ringtones and they knew that um, there was something with digital music and Napster and all that stuff was starting and big companies are trying to figure out how to be relevant and so that was a super interesting gig. And then AT&T got acquired. So out of all my startups I've worked at, you never think of the big companies the one that gets acquired. So that group got dissolved and so I went on tour with my band at that time. So I was a drummer and uh, got endorsement deals and booked the tour and learned a lot about sales which was what Opened the door to Silicon Valley startups. And so then I was a BD hire at an early stage company and then was a product manager for AOL Mail. So went back to a giant company, left there to start my own company, which was, um, a gratitude software tool for healthcare. And then after that went into drones. So I was business development, partnering with product management at a, uh, drone startup that started in Silicon Valley and moved to Bend. So they had a manufacturing facility here in Bend, Oregon. And it was an Air Force Academy classmate that was coming up here to open the facility and just kind of stumbled across it as I was shutting down my startup. He was trying to build that out. And so ended up working with him to, uh, grow that, which was a fascinating ride. Um, and then when that ended, I got hired to be a product manager for Amazon, uh, working on their drone, like Amazon Prime Air. But that was in the era where. So I meant, I mentioned right before we started. So I had inter. I, I interviewed for a role at Google and I applied to work for you, but then I ended up getting a friend, um, who was at Amazon, told me about an internal job for their drone, uh, drone role that they were looking for. Got hired for that. And then that's when all the layoffs started happening about three years ago. And so after a couple months where they asked to extend my offer, where my start date was going to be, they, they rescinded the offer. And so that opened up the opportunity to where I am now, which is, um, heading up business development, also having our product management group report to me, and running finance at a startup that's based in Florida that makes cushions for people that use wheelchairs to avoid pressure injuries, and then applying that technology to, uh, Air Force pilots. So our first SBIR contract was for the B52. Um, um, because when they fly long missions, they're super uncomfortable, causes all kinds of musculoskeletal problems. And that company is called Calagon. And so all my world kind of combined. So the Air Force stuff came back. Figuring out how to work with the Air Force and a startup on technology we do in house manufacturing, which I learned from the drone company. So the hilarious thing is my career is all over the place. Um, and then I just got picked to speak on a panel at south by Southwest, and the panel topic is Zigzag Having a weird career Career. So it's all kind of come full circle.

Speaker A: Wow.

Speaker B: Yeah, so that's my back.

Speaker A: I thought I had a zigzaggy career, but you definitely do. Wow. That's so amazing. Um, I kind of feel like each of those pursuits could be, like, an amazing substack post, by the way. Like, yeah, it's, uh, you're living kind of like the liberal arts life. Like, really every angle.

Speaker B: Yeah, I love it.

Speaker A: Um, and doing at a really high level. So kudos to you. Uh, coincidentally, I. I actually took. In the spirit of, like, lifelong learning, I took an intro to drumming class a few weeks ago.

Speaker B: Oh, no way.

Speaker A: Oh, my God. My brain was, like, fried after.

Speaker B: What kind of drumming? Like, drum set or, like, hand drums or what kind of drumming?

Speaker A: Drum set.

Speaker B: Yeah.

Speaker A: And, uh, you know, because it looks so fun and I love listening to music, but, my God, trying to kind of have, you know, different parts of your body go at different rhythms and stuff was just, um, something that my brain, I don't think had been trained to do in the past.

Speaker B: But yeah, after. After the tour ended, I taught kids drumming for a little while. And I would say I don't know how they were teaching it, but if you're trying to go too complex too quickly, it's not fun. What I learned from my drum teacher early on, that I think is the best way to learn is put music on that you like and just start with, like, the bass drum and. And feel where. Start as simple as feel the beat and then add there. And don't try to do all the coordination at once. Just enjoy whatever it is that you can feel with the music, and then it just grows much more organically from there.

Speaker A: You know, I think that approach would have worked better for me.

Speaker B: Do they try to teach all kinds of complex patterns? To start, we.

Speaker A: Not right in the first few minutes, but by the end of the lesson, we were doing, like, multiple, you know,

Speaker B: the hot hat going.

Speaker A: Yeah, yeah, exactly. And I, I just felt I. I actually didn't take another lesson after that

Speaker B: because I was just like.

Speaker A: Well, clearly, like some people, it just comes naturally to them in the first lesson. Um, but there were moments. There were moments where I was, like, not thinking about it anymore, and that was kind of magical.

Speaker B: Yeah.

Speaker A: You know, I guess you could argue the same for onboarding new people to a team.

Speaker B: How so?

Speaker A: Like, if you ask them to hit the ground running versus, like, okay, let's. Let's kind of get them into the groove and, like, get them something, you know, very doable and then layer up on top.

Speaker B: Yeah, that's, um, true.

Speaker A: You could argue as a manager, like, maybe you'll have, um, more successful onboarding of teammates that way.

Speaker B: I don't Know I hadn't thought about that. Out of all my parallels that I put together, I didn't really think about it.

Speaker A: Ah, there we go. We got another post. Ready to go.

Speaker B: Jump Shake Theory. So originally my title, so I just started the sub stack and I was going to call it Touring to Term Sheets with the parallels of bands um, to startups and it was my 17 year old son who was just like that's stupid.

Speaker A: Yeah, is way more memorable. I. And um, you could go in a lot of different directions with that. Awesome. So uh, by the way, did you say you were a full time coach? Tennis coach as well?

Speaker B: Yeah.

Speaker A: Oh my God. Wow. What haven't you done? Unbelievable. So maybe we'll talk a little bit about the transition to biz dev because I, I think there are PMs who work with biz dev folks and we kind of think like oh, those are the deal people. Um, but they may not really understand like the perspective of the biz dev professional. Uh, what was your kind of first foray into biz dev like and you know, what do you think people should know about that function?

Speaker B: Yeah, I think so. There are just like product management, there's a spectrum, right? There's the very technical PMs and then the more business PMs and then there's a range in between. I feel like business development is similar where you have just your deal makers and their job is just sign the deals and don't think more strategically. Um, I don't think that ever works well at a smaller company for sure because it has to be such so much more of a collaborative process because what deals you do really determine where you focus because you can only do so many things, right? And so in my first business um, development job at a business school I worked at AT&T where that was a little bit more clear in one way in that they had these prepaid phone cards and they, and they're. It was open ended in that they said we want to do something with this but we have relate. They already had relationships with all the retailers, so Best Buy, Target and Walmart. Um, they weren't really working with the music labels yet, but there was an opportunity to do deals with, you know, Sony Music, Warner Music. I was living in LA at the time and AT and T was in new. Um, and so I would split my time between the two. But what we were going to do, what kind of deal really was dependent on what product we wanted to build. And so what that could be is where it overlaps with product management, right? So and when you have customers and you're listening to what your customers want, there's that intuition around you want to meet your customers needs, but know when to push back. When they don't know what they need isn't necessarily the product you should sign. So if you're just a deal person, you want to sign the deal, it could be easy to um, to just sign the deal that you think that they want. And so that's where business development is also different than sales. Right. Sometimes people will combine those sales is about how much you can sign. Can you grow it fast? Bd I think is so much more important to be slow and thoughtful and it's the deals you don't sign. So the one example from AT&T that I, uh, always come back to when people ask about it is I got to go to Bentonville, Arkansas to meet with the music buyer at Walmart. And I'll never forget, I was pretty young at this point relatively, I guess it was like early, early 30s. And you got this old school Walmart music buyer and he said, I want a country ringtone card. Because it was, they wanted these prepaid ringtone cards and country music is what sells at Walmart. And and so if I were going to just wear a sales hat, I would try to sell them that because that's what he wanted to buy. But uh, understanding the end user and the product we were going to build, I don't know if you remember at the time, early ringtones were just a beat. There was no music. And some people now even remember ringtones. But so for the people who've never seen a ringtone, you could like customize your little flip phone and make it ring a certain way. But almost every country song has very similar beats. And so hip hop at the time was what was selling the most ringtones because it was all around the beats, right?

Speaker A: Yeah.

Speaker B: And so it was a beady role, but it was very similar product management because you could argue about it or you can run an experiment. So the way I got the deal done was I tried to tell them, you don't want a country ringtone card, you want a hip hop card. He's like, well, hip hop doesn't sell at Walmart. And I'm like, but hip hop is the product you want. So we just. What's cool about doing BD or being entrepreneur at a big company is you've got the resources. So I just, I was able to say, why don't we just do both? Let's run an experiment. Because you could debate until you're blue in the face but you don't have the data. So we actually ran an experiment with three different types of ringtone cards. We did a country music card, a hip hop card. And then my theory was people don't buy music based on the genre. They buy it based on a band that they like. And so that's when I did a deal with Warren Music. They had, uh, there was a band called Simple Plan. They were like a pop punk band at the time. And did you ever hear of Simple Plan?

Speaker A: I don't. What song were they known for a particular.

Speaker B: They're a one hit wonder. I'm trying to think of the song right now. But they were, they were kind of popular at the time and they were in the studio. So what I, the deal I came up with there was get them to just record like, hey, this is so and so from Simple Plan. Pick up your damn phone. Like just super silly stuff at the time. But people liked it and their album was coming out and it was going to be on the end cap at Target. So then we also went to Target and said, can you put this ringtone card, that's a simple plan card, their music, their voice with their album coming out and sell that on the end cap. So that also is similar m to what I've experienced in any different role I've had in my career, which is someone says you can't put that on an end cap. And the question that I always say is why? Like why? Why not? Well then you just keep going deeper. And that also I think is the similarity in my mind for BD to product is that curiosity of what's driving it. Sometimes you, they can't, sometimes there's not a good reason. And once you get to the bottom of it, you can run an experiment there for a period of time. So we had that card on the end cap and guess which one do you think? What was the order for those 1, 2 and 3? What do you think was the order in success?

Speaker A: Uh, I'm thinking the Simple Plan end

Speaker B: cap combo kind of teed it up and then what was second?

Speaker A: Second? Ah, I don't know, maybe the hip hop. M. Yeah, country.

Speaker B: And had I just done BD from a sales perspective, I would have just sold the customer what they wanted, which was a country ringtone card, and it would have bombed. And then people would have said, well, this isn't really a successful product, but you, um, didn't sell the right product. And so that's where um, I've Done it in a bunch of different ways. But that's one example where I feel like BD and product, when you're looking at something new is very similar.

Speaker A: Yeah, that's right. Like, uh, I think some folks think of BD as very transactional. Like, okay, yeah, we're gonna do a partnership with this company and that that's done. And they'll negotiate something and come up with a term sheet.

Speaker B: Yeah.

Speaker A: But what you're describing is a much more creative, explore, exploratory, kind of organic process where. Yeah, uh, it is like building a new product, frankly. Yeah.

Speaker B: And that's, and that's where I am like now. So I'm working at a. So Calagon started with Air Force, but then when we were at. I was blown away. We went to ces, which is huge. Have you been to CES recently?

Speaker A: I've not, no. Is it still like ginormous?

Speaker B: It was kind of crazy. So I last went there like 20 years ago when I was at like Radar was um, the first mobile photo sharing app. So that's where after. So I did the AT and T thing, I went on tour and then I was BD higher at a Silicon Valley startup. So it was big company BD and then really similar at a 12 person startup. So that we went to CES. And then when I went back 20 years later, they had this big sign, it was 100 year anniversary and they showed what were the technologies at this huge wall showing the technologies that were like the big thing of that year. And so way back, even before our time, there was like the beta, VHS like thing that came and then there was cell phones and then There was this 20 year gap where I'm like, what's been going on in technology since I haven't been here? And so it went all the way like through that era. And then when I was there, um, last year, it was crazy. They had like John Deere tractors and um, so they had huge areas and cars were really big. So when we, we had a little booth in the startup area and it blew me away that major companies are coming through there looking for startups to find new technology to work with. So Hyundai found us like two years prior and we did um, a deal with them where we put our tech and I'm allowed to talk about this one, we put our tech into a, uh, Hyundai Palisade and then went to Korea and demoed it, um, for their executives. And this is another example where BD and product, especially at an early stage company, are so tied. They Were excited. They wanted to do a deal, but we could not do that deal as exciting as it was. But it's because it's so different right now. We make custom wheelchair cushions where it's manufactured. We can turn it around in seven to 14 days. Each order is really specific. Um, that's so different than doing mass market. Low margin. We're high margin, low volume. That's high volume, low margin. And if I was going to just try to do a deal with Hyundai, that sounds great, but that could have crushed our company because it's a totally different business than what we're in right now. And so we went back then another year, and there's like, a major motorcycle company that found us. And that's interesting, right? It's still automotive, but it's much smaller volumes. And, um, so trying to figure out where you can take your technology next. So that one is like a maybe. Right. And then the third one that found us there was actually. No, they didn't find us there. I'm sorry. This is one where I reached out. So, um, we do very little outbound bd. So that's another difference with business development is how much outbound do you do versus what comes to you. So there's a whole. That's another whole conversation. But on this one, we realized those weren't good things to do. So now you put your product hat back on and what makes sense to us as a company. And we were getting certified with the Air Force for aviation for the B52 cushion. So now what's closer to that? What kind of deal do we want to do versus waiting to see what comes to us? Collins Aerospace is, uh, a tier one supplier for seats for commercial aviation. So now we've been working with them on figuring out how to put our tech into commercial aviation, which is much closer to the work we're doing with the Air Force. And so now it's a slow process because commercial aviation moves really slowly. We're working with them for a couple years. So the startup pace versus commercial aviation is really, really different. But it's still trying to figure out what's the right deal at the right time. With the product roadmap that you have internally, the things that you're already building is a really tricky dance, I guess. Um, and then with investors, it always looks flashy. Right. For a business development deal, which logo do you have? And not being sucked in to take that if it isn't necessarily the right place to focus your limited engineering resources.

Speaker A: Yeah, that requires, um, a lot of Judgment and confidence to actually say no to a logo opportunity.

Speaker B: Exactly.

Speaker A: Especially like early career people, they want to be the one that landed that. The deal sounds pretty awesome.

Speaker B: Yeah.

Speaker A: Um, and what you're talking about is you're, you're kind of looking through like, okay, well, what happens after that deal gets signed? Like, how is that going to set us up for success? And, um, it's a. I guess at the time it probably feels a little riskier, like, well, I'm going to turn down this bird that's kind of in hand.

Speaker B: Right.

Speaker A: And, and wait for something that's, that's, that's a better fit. But you risk like not having any deal this year kind of thing. Yeah, yeah, that's, uh, that's, you know, a similar thing on the PM side that I've noticed is the features that you don't build. And you know, everybody wants to ship a lot of things and now it's so easy to ship features that, uh, you end up with these like, Christmas tree products where it's like a bunch of stuff there. Yeah. And, um, it is hard, it is hard to not launch something because the counter argument is like, well, let's just see how it goes. Right. But to your point, there's a, there's opportunity cost and then there's the ongoing maintenance and then eventual deprecation costs. Um, and user experience.

Speaker B: And user experience. Do you use RAMP at all for, uh, expenses? Have you ever seen ramp?

Speaker A: I've seen it, yes. I've used. Actually I have used it in one previous, uh, job. Yeah.

Speaker B: So we switched to it from bill.com and it's. So now I'm also running finance, which is another, another story. But, um, it was great when we started, but they raised a ton of money. I'm sure they dumped a bunch of resources on it and they just keep changing features and moving things around and the, the user experience is, is jumbled. It still works pretty well mostly. But when you think about what's the primary use of this. There was a. There at one point, there was, um, at the end of the month we tried to transfer money from like the investment account to the, to the business account. We're going to pay the bills. And it like every day. I kept saying it was going to move later and I realized, oh, they're playing with your money. Like, they don't actually have it to transfer. Like, and now we need it to pay bills. And before that it was moving quickly. And I'm like, that, to me is another example of it doesn't Matter. All these little features you can push out if you can't do the primary function, which is allow me to access my money when I needed to pay my bills. Like, that's when you start to lose your users. Right. Like, it made us start to think about, is this a place we want to still keep our money?

Speaker A: Wow. Yeah. They. I do. I think you are pointing out like they raised a bunch of money.

Speaker B: Uh-huh.

Speaker A: And then they added all. Probably hired a bunch of people. And those people, like, their natural muscle memory is to ship stuff, shift stuff.

Speaker B: Right. But are you shipping the right things? Are you focusing on the right?

Speaker A: Yeah.

Speaker B: Ah, the right.

Speaker A: And it's sort of like the new cook who gets all this, like, new kitchen appliances, and then they put. And you're like, wow, you know, like, a simpler dish probably would have performed better.

Speaker B: Yeah.

Speaker A: But, um, yeah. And I want. I do wonder, like, the economics of software seems to be evolving such that before it did cost so much to build new things that you were forced to be more judicious. M. But now, as the cost to produce things goes down, are we going to end up with every product being, like, 100 features that are okay?

Speaker B: Yeah. Seriously. So, like, how do you decide? And especially, like, uh, you've worked much more at big companies with lots of product managers, lots of engineers, and they are supposed to be showing, what did they achieve? How do you think you actually get them to recognize the value of what not to build when. I don't know. They never get rewarded for what they didn't build in that situation, do they? No. Yeah.

Speaker A: No. Uh, you don't. You get rewarded for shipping things that had, like to make the chart go up and to the right.

Speaker B: Yeah.

Speaker A: Your natural incentive is to ship as much as you can. Right. And put as many bets out there as possible. But the customer is kind of like the victim of all these experiments. Right. Uh, of course, you know, when it works, the customer will be very happy. But, yeah, it is. Um, I think it's. It's like so many things in life. Like, it's. It's a. It's. It's explained by the incentives. And to your point, the incentives are to ship things that get you promoted. And the best way to do that for each individual is to try as many things as possible. Of course, they should apply judgment.

Speaker B: Yeah.

Speaker A: But there is a point where I remember, um, one of my first projects at Google, uh, my manager said, hey, this product's done really well. You don't have to have a roadmap that goes out Five years for this thing. Like maybe this product is doing exactly what it's doing and it's reached its point of diminishing returns and that's okay. And you m. Should work on another product, you know. But I remember him saying that and I was like, oh man. Like I finally found something that's working really well. Like of course I want to, I want to lean into it.

Speaker B: Right.

Speaker A: But yeah, that, that I don't know if organizations have figured out. Uh, I guess the way you would do it is you. We don't want to penalize failed experiments because then people don't try anymore either. Right. So there's like a balancing act there.

Speaker B: Yeah, but I think it's running more controlled experiments. Right. Versus just throwing a bunch of stuff out there. So like aol, AOL Mail was one of the few companies that I had access to like tremendous amounts of data because when I was there there were still, you know, millions and millions of users. And I joined right after they had done a, ah, redesign Available Mail. So it was in the era of Gmail, had gotten really big, but they were starting to throw a bunch of features out there and it was getting kind of like it started to feel like this is just engineers tinkering and the user experience, like it was fine. But there was an opportunity. Apple had become retro cool again. It had come back around. And so they had hired, um, Tim Armstrong from Google and they had hired all these ex startup people in Palo Alto to like make AOL Mail cool again. Amazing team of really talented people and all these really great designers. And when I joined, they had just rolled out this new redesign. And so I'm like, well, let me see the data. How's it going? And so we had like thousands and thousands of customers saying, I can't figure out how to compose an email. And I was like, okay, this seems like the major function of email. Right? Like, I don't care how pretty it is, they don't know how to compose an email. So the answer I got was, well. And I asked like, are we doing anything about it? No. You know, we don't have the most technically savvy users, so it'll just take them a while to use it. And I was like, huh, I don't know. This goes back to like the judgment thing that you've talked about before. It's like, I don't need to see a certain number of like, there's not a percentage of feedback that needs to go over a certain amount to be able to say that seems wrong. Right. This is email. They don't know how to do it. Let me look at why. So I'm guessing you didn't use AOL mail back in uh, like 2012 era?

Speaker A: 2012. No, no, but I mean a fun fact. In 2005 I worked on Hotmail.

Speaker B: Oh, no way. I didn't realize that. That's awesome. It did have a Hotmail account back in the day, but uh, yeah. So they're at the top of it. What they had was it's a new in one box and then text and im. Because the big feature idea was they can send a text or instant message.

Speaker A: Yeah.

Speaker B: But I was like, well why does it say new? Because it looks like it could be a new text or a new im. They're like, well with the boxes we designed, email was too big. It didn't fit.

Speaker A: Mhm.

Speaker B: Or no, compose didn't fit. That's what it was. They couldn't do compose because that's how they used to do compose a message. I was like, well what if you. They're like, and we can't change the box size because this is already designed. Like, well, what if you just run an experiment or just change. Like if you can make an experiment simple enough where you don't have to debate it. We went from um, new to just email. So then it was email, text and im. And then all of a sudden the confusion about how do you send an email went away. But they were, if you didn't ask why or just be annoyed that users can't do the core function, the thinking was let's just wait and see and they'll eventually figure it out. Um, so I don't know. That to me is just another example of you have a bunch of smart people that have a bunch of good reasons, but you can end up shipping a product to millions of users where they can't do the core function. And that's when, yeah, it's not, it's not going to work. And that experiment was a lot easier. It didn't confuse people. You didn't move a bunch of stuff around. You just took out one word and put a different word. So not every problem is that easy to solve. But uh, I think experimenting, I'm definitely a fan of experimenting, but not, not if it's going to, I guess, confuse people so much to where they can't do the core functionality, I guess.

Speaker A: Yeah, yeah, yeah, yeah, yeah. And I, I think the judgment, the, the system does eventually reward PMs because what I think long term the PMs that move up further and faster, have a higher hit rate. M. So they'll launch something goes up to the right and they'll do another thing. Goes up into the right.

Speaker B: Yeah.

Speaker A: And immediately they, they distinguish themselves. So it's like, oh, okay, well, that, you know, Bob wasn't just lucky with the, with product one like he did. Um, so eventually, like, the system does kind of sort itself out. But you do. I. I would say at the IC level. Yeah. You do have a lot of people, like gambling, like placing a lot of bets kind of thing. I don't know, maybe, you know, that might be working as intended too. Like, um, but you, you, the other thing that you raised was you're working with this kind of, um, really dream team of very capable people on that AOL redesign.

Speaker B: Yeah.

Speaker A: And it took, uh, a lot of courage for you to challenge because I'm guessing they had done designed other products before.

Speaker B: Yeah.

Speaker A: That's all. And they're really smart, whatever. And for you to say, like, well, I don't know, like, are they really gonna figure that? And they had an answer which is like, well, society, blah, blah, blah. So the easy thing for you would have been to be like, oh, okay, yeah, that makes sense.

Speaker B: Yeah.

Speaker A: But good on you. To kind of be willing to have the uncomfortable conversations and have that intellectual honesty.

Speaker B: Yeah, I definitely do that sometimes to the detriment. Uh, I definitely am not a corporate politics kind of person, so I'm very polarizing. Um, after that incident, I also realized we had some vulnerabilities on the security side. So, um, I started digging in a bit into account management. And because there was so much technical debt, AOL mail had been around for so long, they had just had Colin Powell's email. So a bunch of these old school big wig people used AOL mail still. So Colin Powell, who is the chief of staff, like his email m got hacked. So the CEO got called. And so I started digging into why. And there were some feathers that got ruffled when I realized what was going on and what we would need to fix. And so the people on the identity team had been trying to make these changes for a long time, but they had been there a long time too, so they'd only push so hard. But I ended up coming up with a way that we could try to fix things that would make people on the subscription side, there was still a subscription AOL subscription, where it was a billion dollar business. And there was that old school debate over if you make it easy to do certain things, then they might cancel their Subscription. But it wasn't okay to leave it how it was. And so I was the person willing to fight that battle a bit. So I had this army of identity people that were mostly and didn't want to fight, like behind me going, go, go, go. And I had to fly out to Dulles, like, which was very much like old school kind of government, uh, working kind of like people had their cubicles decked out. Like they'd get really upset if they were going to have to move cubicles. Like, it was very entrenched and people didn't want to change. And so interesting. Being willing to fight for what's right is an interesting place to be at a large company. Um, but it is. David Tumkin. Did you know David Tomkin? He was at Google for a while. He was boss's boss at aol. Um, I mentioned to you earlier, so I applied to work for you at Google when, uh, you were in healthcare, and it didn't make it through the massive Google machine. But then, um, David Temkin, who was my boss's boss at aol, saw me doing all these things, saw what I was able to do when I left my startup. And then he was trying to, uh, get me in, um, at Google to work on his identity side. Because there are people that I think in any big company will appreciate somebody that will fight for what they feel is right. But it's certainly not everybody. Like, you have to be okay. I think making some people uncomfortable when you do want to like, take.

Speaker A: Yeah, I guess you have challenged my assumptions about, um, military academies. Because I would have thought, I would have thought that there's a chain of command and you know, you respect the, the orders that come down and you execute. That's not the pattern of behavior that you're discussing, which you know, like, where you're kind of pushing back and saying, like, well, why should we do that? Um, it was. Is there. I. How do I reconcile that?

Speaker B: That's a good question. Um, so I do have to clarify that I am also a fan of like the, the Amazon disagree and commit. I think that is very much a military view. It is your, your job and the expectation that. And they teach a lot of integrity. So what is consistent with the academy? I would say everyone who's gone through any military academy and, um, a military officer is integrity, Ethics. Fight for what's right. But then eventually, once you've passionately, like, fought for what you think is the right thing to do, if the decision is to do something different, you do get in line and you support it and you execute it to the best of your ability. So I have always done that as well. Like I never ever would fight and undermine a decision once it's made. Um, and I think that's the one part of me. I'm not very military in that I don't like guns and I don't like. I'm not, I'm not a stereotypical. I think, uh, I didn't grow up. Like there's, There's. There's a certain kind of Persona people have of people that were in the military that I think is true in a lot of ways that I'm not like that. So I wouldn't say I'm, um, in general, your. Your stereotypical ex military person, but I am in that, I think, fighting for what you believe in. People talk about service. Like, for me, service is also serving whoever you're working for. And if that's the customer, I fight passionately in getting them what I think is right for them. Um, and I think that is, I don't know, does that make more sense that, like, when you think about, disagree and commit that your job is to be passionately trying to do the best you can for the people you're serving?

Speaker A: Yeah. I mean, that's a very first principles, like, mission driven way to look at it. And it makes a. It makes a ton of sense and I think that's super healthy. I. I hope that that's common for, for everybody. Um, let me. Let's talk about the, the hiring thing, because rarely do two people meet.

Speaker B: Yeah.

Speaker A: They were on the other side of the thing where it didn't happen and like, oh, what happened? So you, you reminded me before we started recording that. Oh, hey, uh, did you know I applied for a dollar? So like, walk us through. Yeah, your, Your perspective and then I'll share the backstory and then it'll fund the trade notes.

Speaker B: Awesome. Um. Um, so I had been working at my startup for six years. It was called. And you pronounced it better than me. So I said doje. It's a phonetic spelling for thank you in Cantonese. So how did you. Earlier you said, how would you.

Speaker A: I said dodger, which is like the Cantonese pronunciation, but I understand why you. You know, that's hard for people.

Speaker B: Yeah. But thank you for saying it the right way. So it's, uh, it was a gratitude tool where I had been in the hospital twice and I had a nurse who wanted. Who I wanted to thank, and I didn't thank them when I was there until after I got Home and I have a really good friend who's a PICU nurse, the uh, kids ICU nurse. So I asked her, what do people do to thank you after they leave the hospital? And she had said they can bring cookies or, you know, leave them at the floor. And I'm like, well, do they, do they know that you got them? Does their manager know? What an amazing job. Because these two times I had someone go so far above and beyond for me that I wanted to make sure they knew how much I appreciated them, that their managers knew how amazing they were. And I was like, cookies just isn't going to do it. And so, um, so an amazing full stack developer I worked with years ago, his parents had been sick and so I reached out to him and said, I don't think this is a business but it needs to be built. And so we started out just creating a tool for patients to thank healthcare workers. And we got UCSF Benioff Children's Hospital to be our first, um, kind of pilot customer. And so then they had been working with a company called the Studer Group about peer to peer gratitude and they were writing handwritten peer to peer notes. So, so they asked us if we could incorporate that. So we ended up building this whole gratitude platform where people can thank each other. It was all about authentic gratitude. And then managers could see it and recognize them. And it worked really well. We ended up working, got um, a deal with Kaiser, um, and did another pilot with them. Worked with University of Michigan, we were talking with Stanford and so over this time I learned a lot about healthcare, but it wasn't traditional healthcare. And when I was trying to figure out what I was going to do next, someone sent me a link that said, hey, when your classmates is the director of product management for Google Healthcare, they're hiring a pm, you should reach out to him. And so I was like, well, I don't fit exactly, but I have some experience more recently in healthcare, kind of understanding what's going on. It would be at least worth a conversation. So I think I may have pinged you on LinkedIn. And then I also directly applied and the recruiter got back to me, we had a conversation and, and she said, man, your background's super interesting. Like we had a really great conversation. She's like, but we're at this stage now where we're hiring for very specific skills, not looking for like you mentioned in an earlier conversation with someone about people used to hire athletes. You could be a great PM if you have judgment, if you can jump in and work with all kinds of different people. But we're at a stage now where you want this deep expertise. And so normally, with my BD and entrepreneurial hat, I'll keep pushing. Um, but when she said that you didn't even want to have a first conversation with me first. You have the bruised ego, right. Of like, man, I've been pretty successful in my life, and this is a classmate, and he doesn't want to talk with me. So I had to think, like, do I push? Because I probably could have gotten directly to you or through friends, but in my mind, there's an opportunity cost of that as well. If you're looking for at that time is that deep expertise, then I would rather go somewhere where who I am is what they're looking for. And so I actually didn't push to follow up with you. So then what's hilarious is when I put out my drum chick theory substack post.

Speaker A: Uh-huh.

Speaker B: Being true to who I am and all of my crazy, weird, different background, that's when you reached out to me to talk. And it reinforces that if you, if you do you to the best of your ability, that's when I think the world works out. So now I'm really curious on your, like, from your view, would you have ever even considered an unconventional PM hire in that role? Or was I right that it wasn't worth my time to keep pushing?

Speaker A: I think had, uh, you kept pushing, I definitely would have said, oh, yeah, let's catch up. Like, yeah, I actually remember, uh, I think we had. We're in an EC class together. I remember you always having, like, a very clear point of view on stuff. Um, so I definitely would have talked, you know, reconnected. I think the actual. But the hiring decision wouldn't have been the same. Wouldn't have changed.

Speaker B: Right? Yeah.

Speaker A: So you would have paid some opportunity costs. Yeah. And it wouldn't have resulted in a different outcome. And the reason was, uh, when I joined the health team, I was coming from YouTube, so I was like, cat video guy, working, eating, like, clinical product development for Google Health. And so I was like, man, I, uh, need to get some people who know EHRs and health data, ah, and enterprise health, like, inside and out. And we ended up hiring a person who worked for, like a decade in healthcare and had built electronic health record, ah, products from scratch. And, um, that was like, ticking the box that we needed. Um, and so part of the other thing that comes to mind is, uh. And actually someone said this to me, uh, a couple years ago when I was looking at a, at a role and I didn't get it and he said, tom, you and I are too similar. And I was like, wasn't that a good thing? Like the same language, but now like, yeah, no, he, you know, sometimes the hiring manager needs to find a compliment.

Speaker B: Right.

Speaker A: And um, you know, I think in the old days, early Google goal, we would have been like, just hire the smartest people you can and they always figure it out and then you would have been in that category.

Speaker B: Yeah.

Speaker A: But I think now, uh. All right, you know, a few years ago I, I already started to see more specialization, especially at the more senior levels. Like, I see like, you know, kind of right out of B school. Like just go for athletes is fine.

Speaker B: Yeah, but.

Speaker A: And then now with AI, yeah, it's even more extreme where it's like, well, every, you know, everybody with Claude can write a good PRD now so, you know, and they can learn about a new industry pretty quickly just using AI. So what you really value is the domain expertise where they've seen this movie many, many times and they have that extra 5% judgment that's going to be the difference between first and second place. So yeah, like, um, that's kind of crazy how we reconnected after, after many years of this happening. And um. But yeah, like know that I think the uh, Taylor, the recruiter steered you right? Because I think she knew, hey, I need someone who like bleeds ehr. And you had healthcare and you had innovation.

Speaker B: Right.

Speaker A: Um, and you're, you just have like a great background all around. But it wasn't a like fit for purpose, higher the way we were looking for.

Speaker B: And I think it's, I think it's a reminder for anybody. It's such an emotional roller coaster when you're looking for a role at any level and with any expertise or background that like I've shared, shared other ones with, you know, like when I didn't get the itunes job, like putting yourself out there, you. Nobody bats a thousand like you. I think it's similar to like a top hitter, right. If you're batting.300, you're doing pretty well. But unlike batting where like it would be great if you got on base every time, I really do think the old parable of like, it could be good, could be bad, who knows is really true. And you just, you can't, you gotta just have a thick skin and not take it personally. And it's also similar, I think, to college applications you and I had talked about sooner, which is working with any kid who's applying to school or even, uh. At one point in my career, I also didn't mention I worked with, uh, uh, there's an MBA admissions consulting, Stacy Blackman, where she has a brilliant model, where she hires only people who graduated from top business schools to be her consultants. So she does all the BD funnel and gets people who apply, and then she doesn't have to manage them. You get a bunch of type A overachievers and you just give them candidates. And so I got to work with people applying to business school. And it is, it is similar to working with a high school kid. Um, when it's your own kid, it's really different. But there is a common theme, I think, across applying for a job or applying to business school or figuring out even where you want to go as a high school kid, which is the best thing you can do, is just get really clear on who you are. And if that means that you don't get in somewhere, it probably isn't the right place. Place. The worst thing you can do is try to just be all things to all people, because then it's fine. If a place can clearly in a second say, you're not the right person here, that's a win. So I would say me not like Taylor being able to quickly say, you're not the right person. At first it hurts, but then you're like, oh, I clearly was who I am. And then that led me to my role now, which is so much fun. And I'm not, you know, making. I didn't optimize maybe for the most amount of money, but I don't think I would have done as well. I would have been miserable. Like, because when you're not. When you're not in a place that pulls from your core strengths, I feel like even if you can figure out a way to get in, at some point, it's going to eat away at you. And so I think, yeah, it's like for applying for colleges, it's the same thing. Like, if you can get a clear view of yourself, you might not get accepted somewhere, but the place you do much more likely is going to be a place that you're going to shine. And so it's the same with jobs, I think.

Speaker A: Um, I totally agree. And I mean, in hindsight, uh, uh, two or three years later, we restructured that whole group, so.

Speaker B: Oh, really?

Speaker A: After that, anyway.

Speaker B: Yeah.

Speaker A: So you might have dodged a bullet in some ways.

Speaker B: Yeah.

Speaker A: You know, the thing that you're talking about that really strikes A chord with me is for high achieving folks. Growing up, um, I was led to believe that, you know, great winners just crush it on anything they do. Mhm. And I think what you're talking about as well, that at some point in your career, and I would say even early, uh, to your point, like even applying to college, like it doesn't make sense to bat a thousand. Like that's, that's, that's kind of a bug. Like something's not right.

Speaker B: Yeah.

Speaker A: Like if you see these headlines like oh, meet the kid that uh, got admitted to every single Ivy League school. Well, how does he want to go to like Brown? And yeah, like that doesn't make sense, you know, whatever. Um, so uh, I do think a lot of high achieving folks are not wired to accept failure. And if failure happens, the first thing that we ask ourselves is what could I have done differently to change the outcome? And sometimes it's like, well, you weren't meant to go there or get that job or whatever. And it has nothing to do with your value or your intelligence or work ethic. It's just like they needed someone with a different background. That's not what you had. You can't have every background.

Speaker B: Yeah. But early on in your career you, you do what you do. Kind of get everything. Like you are all these different things. And so it um, yeah, it's also like the, when the Lean in book came out, um, I was at AOL and they handed those out to everybody. And so I ended up talking to some other women where it's a great concept and I appreciate where she was coming from. There are women that I think need to learn to lean in. But in a, um, similar vein to like, you can't win everything. You also are going to destroy yourself if you never give yourself the chance to lean out. And then putting extra pressure on people who are already fighting their instincts to like try to have it all. People say like, you know, balance like you can't have. Back in the 70s it was like, you know, you can be this career woman and have it all. But like now I think there's been this shift to. And it's the same for men and talking about with women, but I feel like it's the same pressure, right? Like you can't do everything to the extreme all the time. Something is going to break. And so, um, knowing when it's okay to lean out, uh, knowing when you don't have to keep having grit and keep going at something if it's not working. Like we had talked also earlier about that. Like, you don't. You don't hear enough of the stories of the decisions people have to make to know when it's okay to walk away or take an exit. That's maybe not the huge exit, but it wraps it up nicely and it can carry on in some way or it takes care of employees. But maybe you don't make money or your investors write it off. Like, I don't feel like we see enough of those stories. Um, and so that's one of the things that I've been really kind of pushing on lately. Yeah.

Speaker A: Yeah. I. I think the fact, like, so people should check out drumstick drum chick theory.

Speaker B: Thank you.

Speaker A: Because there's a post there about, uh, when things didn't work out in different parts of your. Your kind of career and. And life experiences and knowing when to kind of say, like, okay, I'm gonna move on. Uh, I think the one that's most memorable is, like, the band, like, the basis and the singer, and then people paying for, you know, trying to undermine your new singer. And I was like, oh, my God, it sounds like a startup. Yeah, yeah, yeah. So, um, I think. I think part of it is that, you know, success is probabilistic, and you could be the best in the world at something. It doesn't mean you're gonna. To bat a thousand, even when it is a perfect match. Right. And, um, you know, I. I. Do you play poker at all or no?

Speaker B: A little bit.

Speaker A: Okay. Well, you know, sometimes if you're in a poker tournament, you got to give up some hands that actually look pretty good early, and then they're not panning out. Yeah.

Speaker B: Yeah.

Speaker A: And if you deploy all your chips against this hand that started out looking good, but now clearly is not looking as good based on all this new information that comes in subsequent kind of, um, you know, parts of the game that the. The smart move is actually, uh, move on to the next hand. Yeah, but that is. That's easier to do in poker than in life, because in life, the cost of saying, like, yeah, we're gonna kind of wrap up the band or we're gonna wrap up this company and I'm gonna do something, or I'm gonna go to a new company or new job or even. I'm not. I'm just gonna, you know, take a little break. Like, that is. We're not wired for that, and we weren't. I think this is, like, now we're getting into, like, parenting. But I do have concerns around, like, achievement culture. And, um, you know, I. I live in Palo Alto and there's a lot of high achieving families here and it's just like, ooh, are we sure that we're setting up these kids for success? To think that they have to be nationally ranked at everything. Like, yeah, not gonna happen.

Speaker B: Yeah.

Speaker A: And what happens when they stumble? And you see this sometimes with new hires that are straight out of undergrad or grad school where all they've had is success. Mhm. And then they, they get on a team and they don't get along with someone and people don't want to work with them. And now you're like, oh God, I gotta have a coaching conversation with, you know, Jane and kind of go over how like being right is necessary but not sufficient. Um, so yeah, it's ah, I, I can't wait to read more of your stuff, Amanda. Oh, thanks you. I hope you. Because you're willing to kind of put it all out there and that's like so refreshing in, in 2026, I guess by the time this gets published.

Speaker B: But I think it's. Thank you. But I'm curious what you think though. Like, so I, in my last post, I like, I don't want it to be just about me. I want to share other people's stories. And so I know two, two founders who recently ended their startups. One is young and one is older, like our age. Um, the younger one took my challenge and wrote his reflections and shared it publicly. And it was really great. I don't know if you saw his. He shut down his company. But then when he posted on his LinkedIn there was a guy who was awful, was like, just bashed him about. You should have known that. And like, how did. Of course, like you should have had that awareness before. And I'm like this. So there is a real. I guess I understand why people are afraid to share because there are people out there that will then attack. And so you're protecting that vulnerability. Um, and then the older person has not shared yet. And I think there's more risk potentially when you've had all this other success of like, what does it mean if you share this? I don't know all the reasons why yet. They're contemplating if they're going to share. But it also is really hard when you've raised money from friends or even just regular investors. And if it doesn't work out, facing that, uh, is challenging. And so my, I guess my question for you is we're never going to change the people out there that will attack. Like this person who put this kind of attacking post on the younger, on the younger kid who shared his story. Um, how do you think about people, people being willing to share? Because there is the value of people sharing these and not feeling it like not allowing those things to get to you or being a barrier to sharing when people do attack like that.

Speaker A: Oh, uh, that's so hard. I think part of it is most people would be more willing to share, um, successes and mixed things and failures if everyone else was sharing similar transparency. But if everybody else is just talking about like, everything's amazing, I just got promoted, whatever. Uh, and then one or two are like, oh, my startup freaking was it didn't work out or like we're wrapping it up. Then, uh, I think the, the concern is the sharer gets penalized and they are like, well, I'm gonna look like I'm kind of not as good as everybody else. Maybe in reality you're basically, you might be better.

Speaker B: Yeah.

Speaker A: But everybody else is kind of choosing what they reveal.

Speaker B: Right.

Speaker A: So there is a little bit of a chicken and egg thing. I think really, um, people who've been around and have great judgment about other people recognize that vulnerability and authenticity as a strength. But maybe, uh, people earlier in their career, they don't. And so you wonder like, okay, is this going to kind of come through? And so, yeah, I think, uh, I think that's a tough one. And I think that's why it's rare to see people put themselves out there because they're like, well, look, I don't. What if the next hiring manager

Speaker B: and

Speaker A: they have another candidate that just looks like they win all the time. Nothing but winning.

Speaker B: Yeah. Yeah.

Speaker A: Then, uh, then maybe that hiring manager will pick that, that other candidate and think of me as some kind of damaged goods or whatever when reality, I'm just the one being honest.

Speaker B: Yeah.

Speaker A: So, yeah, I think, um, I can see why your other, uh, guest is main. May or may not want to share.

Speaker B: Yeah.

Speaker A: Because I think the, the, the thing will be there's probably a way to be open and transparent without like completely falling on your sword.

Speaker B: Right. Right. Yeah, that's a good point.

Speaker A: That's still, that's still good. Like, okay, here are some things that worked and here are some things that didn't work. And this is why I took away from it. Like, I think that type of positioning can be, can be like kind of thread the needle. Um, but it is, it is kind of sad that the incentives are, are not there for people to be open. And me, it's true about lots of things right in life.

Speaker B: I also think even, even if it's not a hiring manager seeing it, it is still human nature to want the win too. Like, I'm not gonna lie, at the startup I'm at now, people are like, why, uh, you know, with all the different things you've done, why are you still grinding at a startup for relatively less pay one it's fun and like lifelong learner. Like, I love the opportunity to wear a bunch of different hats and constantly learn. Like, I'm learning a ton. But there is a little piece of me that's like, like for the startups, like, I've had many little wins. I've had some good successes. I learned kind of a new phrase that I really like, which is looking at a startup as far as which ones. It's an investment thesis of one investor that I guess I didn't hear because most companies don't make any money. But her thing is if you have a series a startup that they have more revenue than dollars they've raised, they're a good candidate for actually having a real business. And so we m. Were like, I knew we were close and I looked at it, I'm like, oh my God, we have more revenue than money. This is a real business that's got a real chance of like growing. It's not just get growth or get users. Like, it's. We're selling stuff that people want and we're making money. And, and there is a little part of me that while I think it's great to have honesty and share when things didn't work out, like, I really want this to be a big win, like those are still really fun too, right?

Speaker A: Yeah, you definitely like, I think we all want those things. The um, the poker analogy is like if you play in a tournament, um, and they pay out like the top, like third ah of of entrance like you, you, if you play perfect, you might win 40 of the time. You might get a little edge because of your decision making, but there's so much variance.

Speaker B: Yeah. Yeah.

Speaker A: In the outcomes that even if you make the right decision, there's a big kind of like luck element to it.

Speaker B: Yeah. Yeah.

Speaker A: And so, you know, most m of us, even if we make all the right calls, we're not going to get the giant Andreessen mega round and then the big IPO on the NASDAQ and yeah, you know, ring the bell and all that kind of thing. So, um, this is just, this is just life. I mean, the other thing is, I also think we are. It's it's not healthy. And I think you and I are, are kind of like we're looking at things holistically. It's not healthy to judge your, your success by like, oh, am I going to be the one that's on the COVID of Business Week or something like that. Like that, you know, you could do all the right things and there's only gonna be a few of those, you

Speaker B: know, and then that's where like, it, you know, could be good or could be bad. It's great. You go to a top business school. But then our classmates are Sal Khan and like, like people are like, oh, you know, Charles Duhig. Like, you know, I want to write a book. But like he wrote Power of Habit. Like there is a level of comparison that you have to get very comfortable with. Just enjoy the journey. Like, enjoy your journey and you can't. There's always going to be somebody better. There's always going to be something to compare yourself to at any level. Right. And you know, you're all, you're always going to struggle if you can't find a way to separate that and not compare. Right. Like, yeah, it's just a very unhappy place to be, if I think so.

Speaker A: Yeah. And then, uh, another, like I was chatting with my sons about this because we, we watch football and they were like, oh, this, this quarterback, like, he sucks. And I'm like, wait, timeout. He plays in the NFL.

Speaker B: Yeah, exactly.

Speaker A: Yeah. Oh, but he's not as good as so and so. And I'm like, well, okay, number one, like there's team, there's scheme, there's coaching staff. Ah. You know, these are just games won by inches. Like all of these quarterbacks that play in the NFL, like, are at the, the most elite level. They can be m. And there's no quarterback that sucks. Like, that's crazy when you think about it. And I think similarly for career success, like, you might already be playing in the NFL. Yeah. But you might not. Like, you're not gonna win like three freaking super bowl bowls in a row. Like, that's hard to do and it's not.

Speaker B: Yeah, yeah, yeah.

Speaker A: And also I think if you try to like, will yourself into changing those odds, like you can start to get to a place where you're, you're not acting naturally in the, in the flow. Mhm. And you're trying to force it.

Speaker B: Yeah.

Speaker A: So I do think there is like, of course you want to leave it all on the field, but yeah, like, if you get too tight and you're in A rush. Uh, then you're kind of probably going to make it worse for yourself too.

Speaker B: It's true. So poker. So do you. Do you actually like, go play like poker tournaments? Like, is that your thing?

Speaker A: I have a monthly game with. With a, ah, few section mates. Okay. So. So we, we play and, and I talk about comparison culture. Like I am the poor man in that group.

Speaker B: Oh, really?

Speaker A: It's fund managers and stuff like that. So luckily we, we play just for, you know, very small stakes. But, um, yeah, I think it teaches you. I try to teach the kids like life lessons because poker is all about making good choices, taking calculated risks, understanding the dynamics of like, multiple signals, and then being comfortable with variants, you know, and life is freaking variants.

Speaker B: And I guess that's. Yeah. That's so interesting because my, My younger son has been playing poker with his dad for years and they have this running tab. He's like, in the whole like billions of dollars because he's so comfortable out on that debt limb. Right. Like, I want to bet it all. And I'm like, you're not learning the lesson that we want you to learn. Maybe there's like, yeah, what do you do with the kid who's just keeps betting it off? Like, ah, uh, I'm confident I can throw another. Yeah, I don't know if he's getting the lesson.

Speaker A: I mean, that sounds like young male brain behavior.

Speaker B: Maybe.

Speaker A: Uh, because I play with my kids, like my youngest, and he's like, I call him Captain Call because he's like, I don't know, I could win it all back this time. And I. But lately he's been, uh. Now he's 15 and I think he's starting to realize because what I introduced was like, well, um, we're gonna. If we want to play, like you're gonna make these decisions, it'll be just for like a couple bucks a hand or whatever, but it'll come out of your, your account.

Speaker B: Yeah.

Speaker A: And so like, you won't be able to go buy yourself like a nice lunch or something or you will based on these decisions. So it's not just like this funny money like, like, uh, uh, you know, pulling like a, you know, casino game kind of kind of thing. This is like you're gonna make decisions. There's results. Yeah, there, there's impact. And think. Think about it. And uh, if anything, the one thing that I thought was good judgment was after a while he's like, I don't want to play you anymore. And I was like, well, you might. That might be A good lesson, which is like, you have to assess your. Your opportunities.

Speaker B: Yeah.

Speaker A: So, yeah, Um, I can't wait to. To. We gotta get. Have you back. Amen. I feel like we just scratched the surface. I know. We promise. I promise you it'd be 30 minutes and we're over an hour, so I pop. So long. But it was so fun catching up.

Speaker B: Yeah, same here. Thanks for having me.

Speaker A: So it's Drum Chick Theory on substack. And then, uh, if you randomly happen to be in a business that requires advanced, uh, seating technology, the company is. Was it Callaghan?

Speaker B: Yep.

Speaker A: And. And how does it. How does it. How does it actually help you? Like, what is the technology behind the seating?

Speaker B: Yeah, so it's a, uh, it's a combination of foam and air bladders and sensors and software, so it. It adjusts the pressure. So for people that sit in wheelchairs, normally, you have to be able to do offloads. So they're supposed to lift themselves up to get the blood flow back so they don't get pressure injuries. And sitting in this cushion, it does two things. It automatically moves the pressure by the air kind of coming and going. And there's an app. So if somebody has an active pressure injury, the part that I think is just amazing every time I hear a user story, if you have a pressure injury, you're often laying in bed for a long time because you can't sit up because it won't heal. And these can go on for years, and they can take lives. And, um, with the app, they can actually remove all the pressure in that area, so they can actually still, while it's healing, get out of bed, get in their chair and live their life and help heal ultimately the pressure injuries so that they don't have to deal with that anymore. And so, yeah, that's what it does.

Speaker A: That sounds amazing. I kind of feel like I want to add one to my Aeron chair because I sit at the desk so long.

Speaker B: Yeah, we always hear this goes back. Going all the way back to the beginning. Everyone's, I got to put in desk chairs. And it's like, we will at some point. That is. The idea is it's technology go into lots of different applications, but if you really look at the use case when you're sitting still and you have to move for them is really different than when you're moving around. And we've tried. I tried sitting in one of our cushions at my desk. And if you're being really honest, it's like, it's not super comfortable in the way it's designed right now for that use case but all the underlying like understandings of ergonomics and how people sit and how to move the how to design. We do all the in house like bladder designing. We've got anyone who loves like machines. We just move from a small little production area to like a three times larger space. And so our CEO is incredible at finding like used manufacturing equipment and then we get like people like newer people in and train them up. It's really cool when people talk about us based manufacturing. We're actually doing that. So at some point there will be office chairs. My role is also helping like let's stay focused.

Speaker A: Yes, of course, of course. And then uh aftermarket like if I have a long road trip I wouldn't mind adding it. Like maybe it doesn't come with my car but I can pay a little you know afterwards and add it on.

Speaker B: And that's one much more than an officer because you are kind of stuck in a position. It really like we have to be in that market. Like we are by far. I think the best option is why Hyundai I think was excited about us. Yeah, um, yeah that's where that's also the struggle too. Do you pour a ton of cash on and really higher up and grow out. But we need. This is where I might come back and pick your brain. We don't have a really deep product management team and if we're going to go in all these different verticals we really need to start having more methodical like product teams, building roadmaps and like getting cost down. And um, it becomes, it becomes a real business that needs to scale. Um and if you try to do it before you're ready the chance. This isn't one that we want to have be the uh, 1 in 10 is huge. Like, like we have enough established that it should be successful that we want to, we want to grow intelligently.

Speaker A: I hear you. Yeah, I think, I think you guys are doing it the right way to be honest. I mean I mean even though I love like new ideas and adjacent markets, I think the risk is you build out a product team focused on like aftermarket automotive or something.

Speaker B: Mhm.

Speaker A: And then you will want to hire a PM that's going to be thinking all day long about it.

Speaker B: So if you have a good like actually with all the people you talk to. If you find opportunistically we don't have the bandwidth to go on a search but if you find an automotive PM. Ah aviation like tier 1 seating PM for commercial aviation like we are totally open to hire. So if there's someone who wants to get into a, a growing company with deep now I'm like the person who wants the functional PM expertise but I do see the value in that um, because we're past having the generalists like to really grow. If you find somebody awesome, send them our way.

Speaker A: Okay, so you're looking for like the person that worked on like seating for Tesla or Rivian or something like that.

Speaker B: Totally. Okay.

Speaker A: Well you never know. I mean there's, I think there's like on um. I'll put this on LinkedIn. There's like 10000 followers so maybe one of them. Awesome. How? And they can reach you on LinkedIn I'm guessing?

Speaker B: Yeah. Mhm.

Speaker A: Awesome. Well have a great uh, New Year and rest of your weekend.

Speaker B: Thanks, you too Tom. Take care.

Speaker A: See ya.

Speaker B: Uh, bye.

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