Ep 4 - Patrick Wetherille - Managing Detractors, Working from Anywhere, and Optimizing our Finances and our Lives

Speaker 1 Hello friends, this is Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.

Speaker 1 So let's get started and get you one step closer to where you need to be.

Speaker 1 My guest this week is a good friend of mine who I respect dearly. His name is Patrick Wetherill and he and I met almost 20 years ago at the London School of Economics.

Speaker 1 I asked him to be one of my first guests not only because I knew he had to say yes as a good friend, but because he has always had incredible instincts for how best to create work and social environments that focused on open, honest, and engaging culture.

Speaker 1 Additionally, I wanted to bring Pat on early in this podcast because he's one of the few people I know who has simply never bought into the idea that deferring life and experience is somehow a good idea.

Speaker 1 Patrick is currently the COO of Ada Health, leading daily operations while shaping the organization's strategic vision to empower individuals in their healthcare journey.

Speaker 1 And prior to joining Ada, Patrick served as CEO of Lose It, one of the most successful apps ever with over 50 million users.

Speaker 1 He drove the company to growth, profitability, and its acquisition by Everyday Health Group, a Ziff Davis company, in 2022, where he served as managing director.

Speaker 1 He holds an MBA from Harvard Business School, an MPP from Georgetown University, and a BA in economics and political science from Haverford College.

Speaker 1 Throughout this conversation, Patrick and I touch on startup cultures, the difficulty of being in executive positions, remote work philosophies, and some books that have truly impacted both of us.

Speaker 1 My only meaculpa addendum is that the audio is not ideal for a first guest, and that's my fault for not getting the equipment out to my guests as quickly as I needed to.

Speaker 1 But trust me, this one is worth sticking around for, especially if you would like some creative ideas as to how we can balance work and life more effectively moving forward.

Speaker 1 And Pat and I touch more heavily on money and spending philosophy as the conversation progresses.

Speaker 1 So without further introduction, I give you my first official guest conversation with Patrick Wetherill. Patrick, thanks for being on the show.

Speaker 2 I really appreciate it. Thanks for having me.
I'm excited to be.

Speaker 1 So can you tell me a little bit about what LoseIt is as a product?

Speaker 2 LoseIt is a weight loss app, one of the first apps ever in the Apple App Store. It launched in 2009.

Speaker 2 It's basically a food lobbying purse to weight loss where people go in, but they enter in what foods they're eating, that counts their calories, and it shows it against the calorie budget.

Speaker 2 So, if someone wants to lose weight, but we give the user a budget, they stick to that calorie budget. It's a calorie deficit that drives weight loss.

Speaker 2 So, it's a very old-school approach to weight loss, the same approach with Weight Watchers. This product was designed when the iPhone came out to make it really easy.

Speaker 1 What was the impetus behind the need for this type of product at that time?

Speaker 2 So, there were three co-founders, Lonov or Regional founder who he had worked with the other co-founders before. He was tracking his food.
He was tracking his calories, tracking his food intake.

Speaker 2 And he had built some kind of software for himself to do it. But then all of a sudden the iPhone comes out and the idea of these apps comes out.
And he was a software engineer.

Speaker 2 So he's like, you know what? Just for fun, I've got to make a thing I could use on the iPhone so I can track my food. I track my intake to lose weight.

Speaker 2 And the other co-founders started interacting with him about it. And we're like, this is pretty great.
This is actually going to be pretty compelling. We would love to work on on this with you.

Speaker 2 He had already had a few good exits. He funded the team.
They put it in the App Store. One of the co-founders is a designer.

Speaker 2 So, if you look at a core of Lusit's design paradigm, it was this guy, Paul D. Crusina, who was a really talented designer.
He made the food lawn really fun.

Speaker 2 But it was one of the first apps ever in the App Store. People were scrambling to catch up to the new paradigm.
Lusit gets out there, the number one health and fitness app.

Speaker 2 And it stayed in there for two and a half or three years. Back then, Apple's Discovery was just the most popular apps list.

Speaker 2 If you had a good position in the top apps for your category, it just perpetuated itself. That was the starting point that Charles Teague, who is one of the co-founders, ended up becoming the CEO.

Speaker 2 At that point, before then, it was one of the people who had been working with them, but they wanted to actually give a proper team really to build the engineering team out.

Speaker 2 And so I joined April of 2012. And then that two or three month period, the team went from three or four to eight.

Speaker 2 And we'd have proper engineers, some of us focused on the Android, a couple of people who focused on iOS. We had some of the viewers doing platform.
I was the only non-engineer that was hired.

Speaker 2 And this is something that even people who are advising me in business school talk to me about. You know, is that something we try to discourage? What is happening?

Speaker 2 If you're an early employee at a startup, you get the worst of both worlds. You're not a founder, so you don't get like founder's equity, but the company is strapped for cash.

Speaker 2 So you're not getting compensated all that well. You're taking all this risk.

Speaker 2 And you're probably better off either starting your own company or go work for a big company that's going to pay you a lot more. And sure, that's good advice, but I'm going to ignore it.

Speaker 2 It ended up being the best thing in my life to ignore the advice. I actually found that I thrived in that environment.

Speaker 2 And what I found is that over time, I was able to control a lot of the company trajectory and being able to go into an early stage startup where I was just hands-on with everything.

Speaker 2 I built a lot of skills and experience that I wouldn't have been able to do if I was at the beer. Right.

Speaker 2 One of the best things in my career was being in a situation where there was way more to do than people to do it.

Speaker 2 And it just meant that I could really pick things that I thought were meaningful and impactful and build experience quickly. I saw peers Myvy struggle to do that.

Speaker 2 They were bigger companies with much more neuro roles, and it was difficult for them to branch out beyond what was their core work.

Speaker 1 Did you have anyone in the company early who decided to take you on as a potential mentor? Did anyone say, hey, Patrick, welcome to the team. Let me show you the ropes.

Speaker 2 The closest person to that would have been the CEO and co-founder, Charles Teed. He was someone I learned a ton from when it came to to starting a company from zero and really around products.

Speaker 2 I didn't have any product experience in the consumer technology space, but in terms of like traditional mentorship of, I did not have that at all. I ended up seeking that out on my own.

Speaker 2 I reached out to alons of my business school, people who had graduated in my year, who were in sort of similar situations. We would share with each other our notes and give each other advice.

Speaker 2 But I never really had such easy spell.

Speaker 2 If you're willing to just try things, figure things out, I think it's valuable, particularly for the the startup world, particularly technology startups where a lot of times the founders don't have business experience.

Speaker 1 I'm really intrigued by this idea of when a startup pivots to the moment where you feel you need a proper team.

Speaker 1 What did you and the rest of the eventual executive team believe were some of the character traits or attributes that you wanted with your proper team to give yourselves the best chance of success?

Speaker 2 At Luza, we thought we needed professionals. We were early on a ragtag bunch of people working on this product and trying to scale it.

Speaker 2 We eventually were going to need some real professionals to do what we do.

Speaker 2 And what we actually found is that every now and then we bring someone in who was a quote-unquote professional, who had typical experience. They were not effective.

Speaker 2 As startups like Lusa, what we really valued was creativity, flexibility, and just a willingness to work on anything coming in with a lot of humility, that willingness to roll with us, entertain our crazy ideas or crazy approach, willingness to just do whatever the company needs of you.

Speaker 2 Even if it feels super junior to what I'm doing now, startups need people who can come in and just roll up their sleeves and get stuff done.

Speaker 2 And so the company struggled the most when we were two of battles. We brought too many people along.
We always looked at Instagram.

Speaker 2 Instagram sold for a billion dollars or multiple, I can't remember what it was, but their team was less than 20 people when they sold for this massive valuation.

Speaker 2 Instagram could do it. We could do it.
Rather than hire more people we wanted to make the people we had more effective.

Speaker 1 Did you ever hire people who within a couple weeks or months, you said, uh-oh, we've got some work to do and we need to develop a support system for this?

Speaker 2 We probably made about every mistake you could make as a startup related to hiring.

Speaker 2 There were some pretty spectacular blunders on our part.

Speaker 2 We did have a couple employees where they came in and they were not meeting expectations and we gave them pretty strong feedback pretty early on and then they stepped up and got it done.

Speaker 2 But there's other times where whether it was a sort of culture mismatch or someone was thrown in the deep end it tended to not be solvable if your instinct is it's not working out or wow this one person's taking up a lot of managerial time because not fitting it's typically a sign that it's probably not going to work out it's never going to really be a good use of your time to support that kind of mismatch right if someone's working in a role and they're very unhappy they hate their work we need to solve that that's not an acceptable state for anyone involved If there's nothing at the company that will make you happy, can the company support you in finding something that would make you happy?

Speaker 2 We actually deal with some really good creative solutions along the way if someone worked for us and was like yeah i'm really dissatisfied in my role i'm just here because i have this incentive and i have to stick around for it it's months away and we're like well it's very solvable how would we call it a burger you just have to wig around for that and we like what you maybe that's called a separance package

Speaker 2 exactly the funny thing is this person didn't think that was even something we would entertain. I'm so glad she said something.

Speaker 2 A lot of times people don't want to say that they're unhappy or they're planning on leaving because they're afraid they're going to just get fired.

Speaker 2 If If I get that, and that's where I think management could really come in and try to create more of a safe space to talk about this stuff.

Speaker 2 Because at the end of the day, we took someone who was very unhappy, a detractor on our team, to someone who was actually very quite happy on the way out and was so appreciative that.

Speaker 2 We were able to solve this for her.

Speaker 1 My least favorite thing I have ever done in my life to date was managing a team of adults. And I don't say that because they weren't good people and didn't have some incredible skills.

Speaker 1 It's that I never figured out how to communicate with the 10% that took up 90% of your time and energy.

Speaker 1 So you could actually focus on the 90% who were doing a great job and contributing to a good culture.

Speaker 1 So did you find any successful techniques that you'd be willing to share of other than severance packages, of how to deal with detractors?

Speaker 2 The most important thing is making sure that the employee feels heard and there's toxic behavior happening, it's in a tab to try to get recognition that something is not going well, something is bad.

Speaker 2 And so that's where I think Mayos Mickey really come in and say, if we want to get feedback, if someone's unhappy, let's hear about why are they unhappy? Is it solvable?

Speaker 2 And if you truly, in good faith, have listened to the employee to try to understand and empathize with that person. That goes such a long way.

Speaker 2 They go from someone who's actively detracting the day to someone who's at least been hurt. Yeah.

Speaker 1 Oh, 100%.

Speaker 1 And maybe this will just turn into the show where I tell all of you how bad I am at all of this type of executive functioning. But how the heck did you stay out of the weeds?

Speaker 1 As an executive, this is easily the hardest thing that I've ever found. And again, my tenure in life as an executive was minimal at best.

Speaker 1 But within seconds, I found that no matter how much you wanted to think about things on the metaphorical 30,000 foot level, you were just brought into the weeds day in, day out.

Speaker 1 So how did you manage to balance the big picture thinking with delving into the minutiae of daily people management?

Speaker 2 Companies in general, small companies in particular, try to do too much. Any given year, we want to do X, Y, Z, all these things.
We're going to try to... Conquer the world in one year.

Speaker 2 There's an instinct to want to do that when you're a small company, you're a startup. We're going to go do it all.
If you try to do everything, you end up not doing really anything.

Speaker 2 But I think for me, the thing that was most helpful on this front was we have very simple goals every year.

Speaker 2 And we took those simple goals and made sure everyone understood what they were and everyone understood how we were going to get to our goals. And all of that.

Speaker 2 So when you're in the weeds, you can't help but see the big picture constantly. The big shift at LuzIt was we were very product focused for a long time.
There was no revenue early on.

Speaker 2 It was all about we want the best products. So we get the most users.
We'll figure out monetization later. I always want to make sure our product is always the best.

Speaker 2 You need a good product. The kind of best product is even better.
But at some point, you have to start generating revenue.

Speaker 2 And sometimes the product experience would be intentionally making money because, guess what's not our experience is having an advertisement to buy something.

Speaker 2 But it was a slow process getting the whole team on board. And so one year we just basically had to say, you know what? We're just doing conversion.
We're just doing things that drive conversion.

Speaker 2 Unless it drives conversion, we're going to be like, why are you working on that? And if there's something that could drive conversion, we're going to say, why aren't you working on that?

Speaker 2 And so there was a simplicity to it. Those are the marching orders.
And it took probably about 18 months to get the team fully converted over to that way of thinking.

Speaker 2 But what we eventually got there, we worked in these, we follow them circuits. They're two months long.
And we go in and we decide what we're going to work on for the next two months.

Speaker 2 And people would be pitching all sorts of things. And it'd be really easy to say, hey, that doesn't drive revenue.
Guess what? We're not going to do it.

Speaker 2 If you'd be like, why now? This is so great. It's because it doesn't drive revenue.
That simplicity was so helpful.

Speaker 2 In my mind, that was the thing that made it really, that was the easiest, simplest, most elegant way to get to a menu that we stayed on big picture.

Speaker 1 When you are talking about these goals, right? It makes a lot of sense to say that once the goals were in place, we knew what our marching orders were. Who came up with the marching orders?

Speaker 1 And what did you do when, potentially as an executive team, you disagreed on the marching orders?

Speaker 2 Typically, what would happen is we'd set the goals. The executive team would need to align on what that meant.
And so lose it was probably a simpler case because we basically had one product.

Speaker 2 And so the marketing worries were, well, we have to drive revenue. We have one product.
So guess what? This product has got to perform better. And there's a lot of different ways you can do that.

Speaker 2 You can do so, you could try different prices, you could try different promotional strategies. You could add features to try to get more people to convert.

Speaker 2 And what was nice is that we generally took the view that we don't really care which one we do. We're willing to try any of them.
We'll test it. We're not saying we would do it.

Speaker 2 We just want to know if we did, would it be effective?

Speaker 1 I'm reading that will never work right now. It's the origin story of Netflix, and it's told by Mark Randolph.

Speaker 1 And he echoes that sentiment and says, all of us are egotistical ding-dongs when we tell people we know if an idea is going to work or not.

Speaker 1 He said the only way we ever knew at Netflix if an idea was going to work was by putting it into practice. You describe yourself as a quantitative marketer.

Speaker 1 Can you tell me a little bit about how that pertains to what are the data points or what are the metrics that you personally would bring to the company to either say this was successful or this was not?

Speaker 1 And maybe something, obviously, revenue is one of those factors, but what were some other things you thought through that you wanted to look at and that you wanted the team to look at?

Speaker 2 It's so specific to the product experience you're talking about. Most health apps are.
things that help you lead a healthier life. And most of it is work.

Speaker 2 So if you want to lose weight, walking all your food every day, that's work. You know what's easier than that? Not beating,

Speaker 2 eating whatever you want. So what happens is you look at retention and it would tail off.
You go through the first week or so and the retention curve was brutal the first week.

Speaker 2 By the end of the first week, you level out and the people who are Instagram will see me around. And so that's where we actually shifted our focus.

Speaker 2 It used to be, well, people use the product or convince them that it's a good product. And then we'll get them with the upgrade and say, hey, this could be even better.
Two things happen.

Speaker 2 One is, like I said, it's lower users at that point. And two, they're succeeding without paying you.
So they've already realized they don't need to pay you.

Speaker 2 They're imagining what it's going to be like to use the product early on. So that's the time to say, oh, we should upgrade now.
Look at all these things you're going to be able to do in the future.

Speaker 2 That's what the consumer health industry is built on, especially gyms. If you were like, you can come join a gym and we're going to ask you if you want to pay us a month after you start using the gym.

Speaker 2 It'd be great.

Speaker 2 But once you show, you lock yourself in.

Speaker 1 Gyms love.

Speaker 2 empty gyms. They love getting a lot of people who are a member of a gym that's empty all the time.

Speaker 1 So did you ever gamify it in a way of this will work, this will keep people on, here's an incentive to keep retention and to lower churn rate?

Speaker 2 We gamified the day-to-day where you could get streaks, get logging features for the day, mark the day as complete. You could build these streaks over time.

Speaker 2 We had some moderate success there, very minor. The thing that actually did move the NELL retention for us was we changed our onboarding.
We asked people more questions in onboarding.

Speaker 2 And what was interesting is that we were getting people to give us more information on what their goals were, more about themselves.

Speaker 2 What we found was that someone's put all this time in, like, I've done it, so I might as well use the product now.

Speaker 2 People felt more like they had, maybe they had invested the product, so they were more likely to come back. And then the second thing, if you're asking someone, hey, do you want to lose weight?

Speaker 2 And they say yes, you're basically getting a very cursory version of their approach to weight loss.

Speaker 2 If you have them answer 25 questions about the reason they want to lose weight and what it's going to be like when they've lost the weight and what their diet choices are, they've mentally thought about their weight loss plan in a different way.

Speaker 2 You've changed the way they're thinking about what they're trying to do. And that change of mindset actually can make people in a better state to want to keep up with something.

Speaker 1 If you were to look back on your time there, would you have done anything differently throughout your tenure as one of the leaders, whether it was from early onboarding and hiring to scaling and marketing?

Speaker 2 Did not push as hard as I think I should have in terms of trying to drive revenue, get more users using premium. And there was one year in particular that we actually had a pretty big setback.

Speaker 2 Apple was rolling out a new operating system and it was a big design paradigm change for apps. It was all the style and everything was going to be different and icons.

Speaker 2 Apps were, they were told that's what it was going to be. They often went through and redesigned how their apps worked, as did we.

Speaker 2 The product team conveniently left out all the promotion we had been stacking in over the past year. They launched the new product and revenue basically just dropped.

Speaker 2 Conversion rate was completely reset to where it had been a year ago. And it took us a year to basically get back to where we had been the year before.
So it felt like a lost year.

Speaker 2 That's what I found the economic ground with our head of product. And he and I teamed up to go to the CEOs.
We've been working on this for a few years now.

Speaker 2 We need to get serious about driving revenue because we want this to be a successful, profitable company. hopefully eventually with a good exit.

Speaker 2 And so we did use that as an opportunity, but we lost a year in the process. It was early in my career.
I was learning a lot. I was really the only consumer business person in the room.

Speaker 2 And I was much, much younger than the founder. but if I had to go back and tell myself something different, I'd be listening to your instincts were right.

Speaker 1 What about the trips to Maui and Cancun and Finland?

Speaker 1 Tell me a little bit about your decision, because obviously I was envious when I heard that you committed to taking your entire team to work, I believe, and please correct me if I'm wrong on any of this, taking them to work remotely on an annual basis for three weeks a year.

Speaker 1 Tell me a little bit about what inspired that decision and what you hope to accomplish with the team on those trips.

Speaker 2 So this was the best benefit the company could ever offer. And it started with the CEO

Speaker 2 with a throwaway line at a dinner with some Apple employees. We went to this really nice French restaurant, the CEO, the founder, he loved sort of French culture.

Speaker 2 And we're sitting around the table drinking some nice French wine. And he says, what'd be great is if we could just work from France for the summer.

Speaker 2 He had a former colleague of his who had moved to France and they were touching. He's jealous because this guy was able to take his kids to school and then work.

Speaker 2 So it was like a really nice work-life balance he had. And so I was like, are you serious? And a couple bottles of wine in.
He was like, oh, man. I was like, oh, I'll look into it.

Speaker 2 I had to work with another person at Arc CEO. She actually did a lot of the library took our proposal together.
But the idea was we want to take the whole company to Paris for the summer.

Speaker 2 And we didn't know exactly what that meant. And we've worked three different versions of it, but he got the proposal.
He was like, this is great. We We should definitely do this.

Speaker 1 Was that the quickest proposal ever written?

Speaker 2 It was very fast. Yeah, it was great.

Speaker 1 On his desk the next day.

Speaker 2 One of the reasons that we thought it was such a great idea was that our philosophy was we don't want people to defer life experiences because you have a job you don't want to quit.

Speaker 2 That's what we're trying to solve for. And it was so positive, too.

Speaker 2 I think the thing that flew to my mind is that there were people who were close to who had never left the United States before in their life, or people who felt it was outside their comfort zone.

Speaker 2 Going into a new culture, seeing part of the world you've never seen before, doing it with your coworkers. So we had amazing improvement in team bonds and connections.

Speaker 2 We have people thinking differently.

Speaker 2 And if it showed up, like the way people were operating, ideas that came up in product brainstorming, and it was great for retention because people felt like, hey, I don't need to quit my job if I want to go to something great.

Speaker 2 And the other thing that really worked is we said, this is not going to be guaranteed benefit every year, but if it goes well, we'll keep it. And we basically had everyone on the best behavior.

Speaker 2 People were really responsible. We gave a lot of lot of trouble.
This is before we did remote at all. If anything, we actually got higher productivity because people were on the best behavior.

Speaker 2 And they're like, we can't lose this benefit. And we did Paris the first year.
Then we did Barcelona after that. We were supposed to do Copenhagen in 2020, but COVID mixed those plans.

Speaker 2 Our kind of backup version, I don't think it was that year, might have been the year after.

Speaker 2 We couldn't really do international, but we took everyone to Austin, Texas for a fall month. I think it was November.
And then the last one before we sold the company was Lisbon.

Speaker 2 And that was actually probably my favorite because it was, we just had sold the company in June. And so we were supposed to go to Lisbon for the summer.

Speaker 2 And I anticipating that we were going to be selling the company, made sure that we like booked everything before, before the coke keys went through. And the money's already spent.

Speaker 2 So I guess you guys are just going to Lisbon for the summer.

Speaker 1 Well, because I learned about this approach that you all took from an Instagram picture that you had put up of your entire team in Lisbon.

Speaker 1 And obviously being incredibly insta-jealous of of what was happening, reached out. You told me a little bit more about that this was actually work.

Speaker 1 And I think this is where what you just said and this whole practice that you adopted doesn't surprise me that it really worked with your team because this is exactly what people, particularly in a post-COVID era, are looking for is stop deferring life.

Speaker 1 And where are the opportunities that are going to give me the room to work and obviously be of use? Did this have anything to do with why you were drawn to Bill Perkins' Die with Zero as a text?

Speaker 2 I learned about that book more recently. I was chatting with some founders in Miami and Cron mentioned this as, hey, this is like their favorite book of all time.

Speaker 2 And I was like, oh, I should read this. And so I read it and basically just devoured it.

Speaker 2 I think I bought five or six copies and started getting to my friends and family to pick up a nutcase being my must read this book. My fiancé was like, I was like, you got to read this book.

Speaker 2 And she's like, I don't need to read it. You talked about the whole book.
You're constantly telling me about everything in the book.

Speaker 1 Could you paraphrase a little bit about some of the key concepts that it offers?

Speaker 2 It's rooted in this fundamental rational economics model of the rational consumer, rational employee, worker. It is you get a job and you are spending money and saving money.

Speaker 2 And you're saving money for retirement. You're anticipating that you're going to be at some point in your life.
You're no longer going to be working.

Speaker 2 So you need to have saved up enough so you can support yourself into retirement.

Speaker 2 And there's a set of people out there who, particularly people who have high incomes, incomes, they make a lot of money.

Speaker 2 They actually end up with more savings than they really need for retirement to build up this pile of assets. And they don't use them in their retirement before they die.

Speaker 2 But what he finds disturbing is that it's not intentional. You don't know when you're going to die.

Speaker 2 And so a lot of times it's just whenever you happen to die, that's the amount of money that goes to your kids. And that's the amount of money you don't get to use for your life.

Speaker 2 Despite the fact that all these tools that could be employed, where he'd said, I want every last dollar of my net worth to be intentionally allocated. I'm going to do it to my kids.

Speaker 2 This is the amount of money I'm going to donate. Here's the amount of money I want to get through before I die.
And there's a lot of people who just don't do that.

Speaker 2 And it basically means that you're leaving something on the table. What I love about it is how much it talks about the value of the experience along the way.

Speaker 2 One of my professors, Henry Spiel Scott, Michael Morton, and he had this book come out right after I graduated called Happy Money.

Speaker 2 And it talked about the difference between b