Episode 6: Finding Opportunity in Crisis with Greg Stewart

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Sean (00:00):
Good morning, everyone, and welcome to our sixth edition of How I Launched This. Today, I am joined by the CEO of a company called Ladder and his name is Greg Stewart, Greg and I have been colleagues and friends for many years. He was in the Salesforce ecosystem, that’s where we originally met, working for an ISV at the time, and has decided to shift out of the Salesforce ecosystem into a B2C technology play.

Sean (00:34):
And I thought, by inviting Greg into this session, we’ll learned quite a bit – both his experience in the AppExchange and what lessons learned he’s applied in his new company, and vice versa, what lessons he’s learned in a B2B space that are applicable to entrepreneurs and product teams working within the Salesforce ecosystem. So with that said, in our sixth edition, I’m very much looking forward to this conversation. Greg, welcome. And thank you for joining and giving back to the overall community. I appreciate it.

Greg (01:12):
Thanks for having me. Super excited to be here with you guys.

Sean (01:15):
So before we kind of begin into the Ladder story, tell us a little bit about Greg Stewart, what did you study in school, what did you think you were going to be when you grew up, besides a tech CEO of a B2C consumer app.

Greg (01:33):
Didn’t think I’d be any of those things. But for college, went to Notre Dame, always wanted to go to school there, grew up going to games as a kid, it was a lifetime of disappointment for the most part, but a great education. Went to games with my brothers in an Irish Catholic family, and that whole deal. But studied finance in college, grew up in a New Jersey suburb of New York and thought everyone just goes in to finance because everybody around you, it felt like everybody was hopping on the train and going to New York for the same job. I think somewhere along the way, I internalized the idea that if you want to make money, you got to go into finance, and if you want to go into finance, you’re supposed to start in investment banking. So that’s what I did.

Greg (02:17):
I started my career at Deutsche Bank in the summer of 2007. I was an investment banking analyst in New York covering media and telecom companies. What I didn’t know when I started that July was that we were starting at the very peak of the market. And on the eve of obviously a massive financial crisis. I remember an MD coming into one of the training sessions and telling us very proudly that that was the biggest analyst class in the history of the bank, which should have been a warning shot.

Greg (02:48):
But I spent two years at DB working my butt off and then one day was told to pack up and and go home, and just people were getting fired pretty much every, felt like, every other week. And I started my career thinking that was just normal. Wow, this is pretty brutal. But after a year of being unemployed, and the worst financial crisis at least in recent history, I moved in with with my wife, then girlfriend ,and thankfully landed at Goldman Sachs, which was extremely lucky from the seat I was in at the time and was extremely fortunate and grateful for a handful of folks there that took a shot on me and that moment would have a ton of impact on the rest of my career and what I would go do after finance.

Sean (03:39):
Were you an analyst as well, at Goldman? What function did you do?

Greg (03:44):
Yeah, analyst, an associate, I kind of give a year back which you’re working 100 hours a week, and you’re sleeping under your desk and doing that whole thing. When I joined Goldman, they had groomed me as a first year analyst, I had to give back a year, but got promoted to associate and spend time in the technology, media and telecom group spending most of my time in consumer internet and SaaS. Half my time at Goldman in New York, and the other half in San Francisco, but I got to work on some really cool deals that are really cool. I worked on Twitter’s IPO, Facebook’s IPO, Yelp’s IPO. Worked on a deal with Zillow, some really, really cool high growth consumer internet companies and SaaS businesses that it was for a moment in time in 2010, 2011, 2012. Pretty cool moment, especially after the crisis.

Sean (04:42):
Yeah, you and I have worked together in a variety of capacities, and I have no finance background whatsoever. I’ve studied English literature, right? And so my skill set from that is really being able to listen and analyze and try to tell a story around what’s happening. When we were doing our prep call, as well as your little notes that you shared around it, it dawned on me that I think one of the things that has made our working friendship impactful is your ability to look at and tell a financial story of a business. And maybe you pick that up in your early lessons learned as an analyst, because you’re able to break down the numbers of the business exceptionally well and then convert that into a story, either a good one or a bad one, depending on what is happening.

Sean (05:41):
So why don’t we jump into Ladder. You’re now with this company Ladder, it’s not a very large company. And that is okay, but it’s starting to have a really big impact. So let’s hear what you guys are doing. This is again, a B2C business to consumer app. It’s a great story and I’m very intrigued by it.

Greg (06:06):
Not a big company, yet, Sean. But Ladder is a social fitness experience for people who are passionate about fitness, but need help planning and maintaining a progressive strength training program. With Ladder, you’re getting a full training program on your phone, you’ve got a coach you can chat with, you have a full team of people and social experiences around you to keep you motivated and excited. Today, the Ladder app delivers the benefits of personal training, but in a very simple, flexible, fun, much more affordable way that doesn’t give up the results that you get by working with a coach one on one.

Greg (06:45):
We do this by delivering world class workout program in our app, delivered fresh every week. It comes with a plan for every day. So there’s no guessing, there’s no random workouts, you know exactly what you should be doing. You’ve got a coach that is there to teach you and answer your questions. We foster accountability, a really important component of what you get working with a coach. You show up because your coach is there, you don’t want to piss off your coach. But we foster that same sense of accountability through intentionally designed social experiences with other people around you who share a passion for fitness.

Greg (07:19):
We do this at a much cheaper price point then a typical personal trainer as low as $39 versus $100 or more per session. But the broader vision is to be the world’s most active social fitness network. This is obviously our first step. As our first step today, we’re focused on a busy millennial who’s serious about fitness, a very sizable group that’s largely been ignored by tech driven fitness and maybe some of the apps that you’ve heard of.

Sean (07:48):
Okay, so in other words, the focus of the app in the service is fitness. You’re trying to connect coaches who build out really cool fitness programs and get your subscribers, in other words, it’s a subscription service to connect not only to the coach and the programs, but also other people that are interested in that same coach and similar programs.

Greg (08:14):
Yeah, that’s right. And it isn’t thousands and thousands of coaches, it’s building very deep networks and communities around a tight basket of the highest quality coaches that are extremely aligned with our team and working very closely with us to deliver the best consumer experience possible.

Sean (08:33):
Okay, so before we get into the story of launching it, and then relaunching it to leverage what we learned from Dan Darcy, in the last episode, who taught us Salesforce never looks at a single launch, they look at multiple iterations of the launch and continuously improving. Before we get to that part of the discussion, let’s pull back and talk about your experience in the AppExchange, where you were selling a B2B solution, and you made a transition to B2C. Talk to us about what interested you in making that switch at a personal level.

Greg (09:15):
Yeah, for sure. I’d like to say it’s some grand plan, but it certainly wasn’t. Yeah, in a previous life I was running an early stage business that built CRM tools for commercial and residential real estate brokerages. It was a product that was built, as you know, on top of an embedded Salesforce license. So a Salesforce ISV partner. The product was purpose built for smaller brokerages and the goal is getting them implemented on Salesforce at a price point that made sense for them without spending a ton of money on services to get up and running.

Greg (09:49):
For me, the transition to consumer was essentially by accident. After the brokerage CRM company, I joined one of my investors in that company and a former colleague at Goldman at a company called Amherst Residential, and Amherst Residential is a huge player in the institutional single family rental arena managing billions of dollars of assets on behalf of smart, large institutional investors. You know, what Amherst had built was a platform that could acquire single family homes extremely efficiently off the MLS and from a computer, rehab them efficiently, convert them into rental properties, and then property manage on behalf of large institutional investors.

Greg (10:33):
So Amherst had built this real estate machine, it was watching the consumer landscape evolve in real time. You know, the companies like Zillow and Opendoor where you’re seeing technology and a consumer first approach, the whole product development and service that was changing industries very, very quickly. And I was hired by amorous to help them figure out what consumer company we can build on top of the Amherst platform. It was a new assignment and initiative for Amherst one that seemed very exciting.

Greg (11:07):
It might might not seem obvious but the connection to the brokerage CRM company is in that means we’ve learned the residential transaction inside and out, which is, you bought many homes, it’s unbelievably complex, it’s very, very difficult to piece it all together. We spent a whole bunch of time really learning the intricacies of what happens on both sides when you buy and sell a house. We were building tools for agents so they could offer a much better experience to their home buyer or seller clients. That knowledge was extremely valuable to thinking through what a consumer business would look like. Instead of servicing the agent to service the consumer now thinking about how it goes straight to the consumer, and offer a really compelling experience.

Greg (11:51):
So I went from b2b to b2c, but the underlying knowledge from one was directly transferable to the other. And during the time at Amherst, we built a consumer business and a brand from scratch in a team called Bungalow, which I could spend a whole podcast talking about. But to keep it short, it gave me a taste of building consumer products and maniacally focusing on the consumer experience with a technology driven approach in an old school industry that really wasn’t set up to be consumer first, or agent first. So a lot of excitement and learnings that kind of sparked an interest in solving consumer problems versus prior life thinking about enterprise software.

Sean (12:35):
Yeah, I love that discipline. I talk a lot from a CodeScience perspective about marketing, better design, better architecture. And when I referenced better design, I mean literally the discipline of UI/UX connecting the problem the user needs to solve, and then from a better architecture, then all the features and functions and data models that need to tie to that direct problem. I think it’s so important to try to get that right to invest heavily in that, and listen, and then adapt and keep iterating on that point, it drives adoption or it kills adoption, and it’s mission critical to commercial success.

Sean (13:23):
You really painted a nice picture of what it takes and why. Why don’t we take a step back? So those are lessons you started to learn as you made the switch from B2C. What about the reverse? What lessons did you learn from working in the AppExchange that you’re now applying to Ladder? Let’s think inverted on that side.

Greg (13:47):
Yeah, I learned a ton from that experience. I learned a lot from you, probably most of it from you. But figuring out how to navigate the massive organization to get what you need, or to get focus from the right person. It’s a hard, requires strategy and thinking and I’ve learned that just they’re doing it and screwing up a whole bunch of times. I learned a ton about sales and the point you just made before solution selling versus feature selling, solving against a problem versus talking about widgets that you built.

Greg (14:22):
I learned a ton about business development, building channel partnerships, partnering with Salesforce AEs, to have them selling our product into real estate brokerages. During the experience, we decided to figure out how to maximize the Salesforce partnership, and it was new to me, and again, you were awesome in that experience to help me get up to speed but we’re this tiny company with absolutely no playbook talking to a behemoth and trying to figure out how to get them to care about us when we had like very, very little to show and very little capital for growth.

Greg (14:55):
So a lot of hustle and then creativity and I think what’s stuck with me, relevant to consumers, is the power of network effects and the power of platform dynamics, which obviously is very real with Salesforce. That definitely stuck with me and something that’s applicable to the ones that we now have thinking about Ladder. I’m sure there’s a ton of other experiences, probably more than I realized, but I took a lot from those handful of years.

Sean (15:25):
Some of the people listening might not know what you mean by the network effect, could you slow down and go a little deeper on that? Some people might assume the wrong thing and the wrong message.

Greg (15:37):
Yeah, and there’s a couple ways I think about it. Where I saw it is Salesforce was able to create a platform that built an ecosystem on top of it, servicing that platform that then helped to fuel growth for Salesforce itself. You add apps and companies being built on top of Salesforce, you had services partners and ecosystems and industries, building on top of Salesforce, which then fueled growth into Salesforce, everybody pointing back to do the same kind of mothership.

Greg (16:11):
And from a growth perspective, and to get to the scale that Salesforce is at, you have to have dynamics like that. A lot of people talk about them. But it’s very, very hard to create and execute. And when you do, it’s very hard to compete against it, and to replicate it as a startup trying to compete.

Sean (16:29):
Nice, nice. Okay, so those are some of the lessons you’re applying, learnings from the AppExchange team, where applicable. How about the inverse of that? What are some lessons you’ve learned on the B2B side, that’s applicable back to AppExchange, ISV, product leaders, product teams, entrepreneurs?

Greg (16:52):
For sure, I think consumer forces you to develop a really, really strong understanding of your customer, a thesis about your customer, an understanding of how they segment, what they care about, what problems specifically you’re solving for them, and how you go find them officially. You can’t compete in consumer, unless you understand this deeply and can figure out how to execute against it, you are hiring a bunch of salespeople, and then hoping that these individuals can use a system to win. You have to create a machine that’s hyper efficient, it’s based on really in depth understanding of who you’re trying to work with, and why.

Greg (17:37):
For me, something that I’ve definitely talked to my team about, if you’re ever stuck or, you’re doubting yourself, just pick up the phone and talk to one of your users. This is definitely applicable to enterprising consumer. But for me, it works every time to either remind you of what you’re doing all the good, or to help untangle what you shouldn’t be doing. And I’ve pulled that lever many, many times in stuck moments.

Greg (18:02):
When I was in the Salesforce ISV ecosystem, I was a young, stupid first time CEO, trying to figure out, go to market strategies and growth. I had a feeling that these things would just happen if you had a better product and you tried hard and you had a good team. I’ve learned through a ton of mistakes that’s just not how it works. Having a great product is required – it’s stakes. But if you don’t have some eggs on distribution, it’s just impossible to make it work, especially as a young company.

Greg (18:38):
I think firing, and you were hitting this a little bit on the design side, but B2B buyers are consumers. There used to be a tolerance for enterprise software, amongst users for like a really terrible experience. And it was software that was being forced down to them from the top of their organization. But enterprise software companies today, those that are explosive have completely turned that approach and that model on its head, instead, focusing on design, consumer design really, but building beautiful, simple experiences you’d expect in consumer software, and gaining initial traction from pools of users who start spreading the product from within an organization because it’s so much better than whatever is being forced down their throat.

Greg (19:30):
Now they got a perfect and obviously relevant example is Slack. There’s a ton to learn from Slack. So in terms of consumer and enterprise, I think from how to think about product development and how to think about understanding your consumer and design. I think those worlds are converging. And really enterprise is catching up to consumer because these people are using consumer apps on the side and expecting now that same experience, ease of use and fun that they’re getting outside of their workday.

Sean (20:01):
Yeah, because it’s not just consumption through one touch point, it’s consumption at desktop, it’s consumption at mobile, it’s consumption at a tablet, it’s a lot more complicated than single threaded. I also think, when you’re selling B2B software, which is the majority of the Salesforce plays, you have to design for your buying consumer, your target buyer, I talk a lot about that. But you then have to show the outcomes the users in your vernacular, the consumers of the app, the people that are actually going to use it on a day to day basis, there’s good quality design for adoption, as well as to drive the outcomes of the business back to that business buyer as the ultimate consumer. Doing that really well is not easy, requires a lot of good design, as we’ve talked about, as well as testing and getting great feedback from your customers.

Greg (21:06):
I’ll throw one more anecdote into that, I mean, the hardest role to hire right now in tech is designing. And it’s really hard to hire or find high quality designers. But it’s hard to hire in general. What we’ve seen is not just startups and consumer that you’re competing with, but you have entire industries and folks that really never thought about design. You can see it in the products and how they’ve thought about producing products for their customers, all of a sudden are caring and are willing to pay up and attract the best design talent in the world and obviously everyone is now competing for that.

Greg (21:44):
So you can feel it, even at the kind of ground up at the designer level that people are paying far more attention. It isn’t just the Silicon Valley VC startups, it’s everyone, because it’s becoming a necessity to compete and to keep your consumers.

Sean (22:00):
Great point. Okay, so I think that we’ve set the table, we’ve got great background. Now let’s kind of bring it back to not only the series objective, which is to share stories about how you launch a product and or relaunch it. In our prep call, we talked about locking in on a theme, in your theme you picked was finding opportunity in a crisis and being challenged with relaunching to fit market fit. I know Dan talked about that in the last episode. I think you’ve got a pretty compelling story to walk us through how to think about looking for opportunity in a crisis.

Sean (22:45):
So to do that, what I’d like to do is I’d like to go back a couple years, you are in diligence phase of whether you’re going to decide to join Ladder. You’re one of the best diligence people I know. Like you’re a former analyst on Wall Street, you know how to break down a business. But it’s one thing to look at things from the outside, it’s quite another to then jump in as an operator, and really get your hands dirty on the business that you are investing your time, your passion, money, everything rolls up into that, your friends and investments, and all that stuff.

Sean (23:28):
So where was the company two years ago? What was working, what wasn’t working and why? Walk us through what you inherited? You weren’t the founder, right?

Greg (23:42):
Not the founder, and diligence, very different types of diligence. It just is like the intro comment for the Wall Street diligence is it’s all packaged up for you. Right? For the most part. Where the company has to get it to you. This is different, it’s early and it’s rough around the edges and it’s not all perfect. The diligence process is very different. A lot more human oriented than just pure analytics.

Greg (24:08):
Yes, I’m not the founder of Ladder. I knew a co-founder of Ladder. A guy named Tom Digan. I’ve known him for 20 years, went to Notre Dame with them. He was a guy who I respected. I knew he was smart, knew he was trustworthy. So you know, obviously followed his career and we’re staying in touch. Tom, like me, started his career in finance in New York, he stayed a lot longer than I did. He was making a lot more money than I was. But Tom was the initial capital of this fitness startup called Ladder. I watched him pack up his life that looked really nice on Instagram, in Connecticut, and move his family, young family to Austin for this little startup.

Greg (24:51):
I was super curious what was going on to make him leave this very successful career and the Connecticut life and New York City and all of a sudden we’re both in Austin building consumer companies. He’s moved on to a completely different path. So I started spending more time with him and after-

Sean (25:09):
Because you were at Amherst at the time working with Bungalow, to go back a little bit. Got it.

Greg (25:14):
Yeah, that’s exactly right. At that time, still commuting every week from San Francisco. A whole other story. But after much more time with Tom, I got excited about the fitness space. You know, I knew it from the consumer lens. Most people can understand it from the consumer lens. But I can see an opportunity was opening from the business side, I could see it was an industry in the middle of transition, similar to what we saw and lived in real estate, in fitness, you can see the focus shifting to the consumer versus legacy power players. You can see technology being introduced into the experience for many. You can see Peloton was proving very clearly and very quickly, that you could build a venture scalable business in this space, which many didn’t believe was possible. And that was all pre COVID.

Greg (26:07):
So I spent a lot of time with the company before I joined. I spoke with some of their investors, I used the product, I spoke with outside venture capital folks that I knew that knew consumer that would have a view on the space just to understand from their lens, what was possible, how would they think about this space. What I learned from Tom during that experience in the company that Ladder was in a really exciting space that had a lot of exciting dynamics and more to the last couple experiences I had. The company had found some pretty unique insights along their path. But they were struggling to figure out product market fit. And they probably didn’t have the right team to do something special for the consumer.

Greg (26:50):
For me that that just felt like a really exciting opportunity. I can see the puzzle pieces were there. And I had some pretty strong ideas on who I could bring with me to help Ladder really become the company that had all the potential to be.

Sean (27:06):
Okay, so in your diligence, you liked the space. But you also started to see pretty quickly, Product Market Fit gaps. Instead of running away from that, you decided to dive into that and re-launch and re-transform the service. Obviously, you didn’t know how exactly you were going to do that. But you’re interested enough and you’re thinking they’re close, but they haven’t hit the market fit bullseye yet. So essentially, is that a good summary of that review and decision making?

Greg (27:42):
Yeah, that’s a good summary, and at least from my experience, when a company in this stage is looking for a CEO, that usually doesn’t mean things are going well. So I think that I think that’s a fair assessment.

Sean (27:54):
Okay, so walk us through the service at the time. I think that’s a very interesting lessons learned that people can pick up on in their businesses.

Greg (28:07):
Yes, for sure. So again, it was in the fitness space, the original business was an app, and that app facilitated online personal training between a consumer and a coach who was an independent contractor. So essentially, the infrastructure that supported an online coaching relationship between the consumer and the trainer. The concept felt intuitive. Maybe somebody will figure out how to build a big business doing it, but we just didn’t think we had the time or the money to figure it out. After diving into the business, we learned it was really hard to retain members. No matter how good the app experience was, no matter what we built from a software perspective, there was still another human on the other side, and how good of a job that human or the coach was doing, essentially determined if a member would stay a paying member with Ladder and consumer gain retention is as important obviously as growth.

Greg (29:08):
And that was a big problem and a warning shot. The concept might feel similar to Uber, you’re the middleman in tech connecting a consumer and a servicing partner. But in reality, we learned that this space had some pretty unique dynamics. It just didn’t feel like these are the problems that were meant to be solved by us at the moment that we were at.

Greg (29:31):
So like with an Uber experience, we think about Uber experience, go from point A to point B, you know the way, time, you know the prices, and the car doesn’t smell, the job was done, it was great. But with the original Ladder app, and fitness in general, there’s just a lot more riding on the human on the other side, how good of a coach that person was, how much they cared, how aligned with our vision they were, how good at delivering online remote experience and tech savviness they were, these are probably solvable problems with time and money, but we didn’t have much of either and just didn’t have any confidence that the business and the one to one kind of infrastructure play was going to be something that we could really take to an exciting place.

Sean (30:18):
Yeah, so translating that story back to make it more applicable to subscription software companies. I get the Uber example, I like it in terms of telling a story. But if we pull back and look at the business at the time, there was a dependency on the quality of the coach and their ability to make a connection to the consumer, which directly relate to your retention rates from a subscription service. If your retention rates in a subscription service aren’t at a proper metric, we’ll call it 90 as you’re getting going to 95%, you literally cannot grow your business because you can’t bring on enough customers, while the other ones are coming out the back door. So whenever you see high retention, sampling is fundamentally wrong with your market fit, you are not hitting the mark.

Sean (31:17):
In your case, it was that dependency between the quality of the coach and the consumer. In the AppExchange, it could be the users, the design, things we’ve talked about that aren’t getting the retention, the renewal, which is so important to a subscription software business. So that’s a broader explanation of what to look for and why and why that is so important to any subscription business. Okay, so we’re locked in on that. Then you take over a team, and you had to make some changes. You had a current team that had designed a certain solution that wasn’t hitting market fit, new CEO, you’re like, “We got to relaunch this, I got to change the team dynamic.” I think that’s so critical in business is getting the right team in the right place at the right time. Tell us a little bit about that process.

Greg (32:15):
Yeah, for sure. I’ll focus on the new team. But the new team or 15 people now. But most of us had worked together before Ladder, some of us have worked together for a couple of companies before Ladder. So we have been to war with each other. This is a group that I felt could build anything. We knew how to work with each other, we like working with each other, we trusted each other. So I brought nine people together across engineering, product and marketing into Ladder and that was a cheat code. There was no figuring out how to work with each other. We can trust each other even, you know, what tools or process to use, we just plugged in and got to work. And that was an amazing weapon at that moment in time.

Greg (33:06):
I wouldn’t have joined Ladder without that group joining with me so I was kind of behind the scenes orchestrating with all these people as a package. You just on this but I firmly believe that it’s always a matter of who before what. It’s people before solutions, or people before executions, and I had a group of people that were capable of tackling any problem as long as they were excited about tackling it together. You know, when you have a group like that, at least what I’ve learned is, you just got to hang on for dear life because you never know if you’ll be able to recreate the same magic ever again. So that was part of my mission was keep the group together and let’s go find something really exciting to work on, on behalf of the consumer.

Sean (33:53):
Okay, so you sell them on the potential. They come on board and now the immediate task is let’s go find market fit, essentially, like oversimplified.

Greg (34:04):
Let’s go figure out a business model.

Sean (34:08):
So we’re here now. Okay, so what did you guys do? How’d you dissect the business and ideate and create something new?

Greg (34:20):
Yeah, the new team came in, we spent a whole bunch of time, efficient time, but spent time dissecting the existing business with Tom, the co-founder. We internalized what they had learned, while the company didn’t find product market fit, they’d learned a ton about the space, about how to deliver coaching experiences, about what the consumer was looking for. Those are all proprietary learnings that were extremely valuable, that we wanted to make sure that this new team fully understood before we decided what to do. Those learnings in that process fueled what we would go build, we knew the one to one personal training app was not the way to go.

Greg (35:03):
But we also noticed that we had a couple of these coaches who were using the existing app and our tools to acquire their own customers, these coaches that build audiences on social media, like Instagram, and they were using Ladder as the infrastructure to turn some of their social following into paying one to one online training customers. We only had a couple of these coaches, but they’re earning the most money, which is pretty interesting. And they weren’t really talking to us. They were just doing all this stuff on their own. We started to spend time with them and we talked and we asked them a ton of questions and we learned that they were using the original app to coach online clients during their downtime. They’re all in person coaches, and they were filling up all of their latent time with online clients and finding those people from their existing social media audiences that they had built.

Greg (35:57):
But essentially, their time became fully absorbed with in person and then online clients in the downtime with Ladder. But as they were clear, there’s more demand there from their audience, and they were turning away potential clients. So it was kind of ears perked and we started thinking about how can we grow capacity for these coaches? What would a one to many experience look like? Do most people want or need highly customized workout programming, or are quality and training style more important, and could programming scale? These are the questions we started asking ourselves and asking our coaches and learning as quickly as we could from them.

Greg (36:37):
We turned that into a couple of experiments in early 2020, where we jimmy rigged the existing one to one training app, so what was here, and we worked with a few of these coaches, who would market to their social media audiences that they were going to train a group of people through an app based experience. What the consumer would get is fresh workout programming every week, not customized, but fresh programming every week. They would all have the info that they would need on the workout, the movement, all in an app. Most importantly, and what was most interesting, we created an experience where these people could talk to the coach and they could talk to each other. So you have someone who’s following a coach, following a workout program in an app with the ability to talk to others that are doing the same program. This first post, a coach threw it out and we helped them create the messaging. She put it on Instagram, and immediately, like literally minutes, turned them into paying customers at $100 a month. They were pre-paying.

Sean (37:40):
This was your pilot. You piloted this.

Greg (37:45):
This was a pilot, yeah. With a really poor experience, it was built. But yeah, it was enough to put it out there. It was our line that we threw out into the water. Through those experiments, and then this is January, February of 2020, we learned very clearly that you could deliver high quality workout programming, in a one to many experience, especially for folks who knew what they were doing, you can do it in an app experience, and that creating these moments between other people doing the same thing. But on their own, it was an extremely powerful motivator.

Greg (38:20):
We saw strangers who met in this app becoming friends. We saw them posting on social media and tagging us, we saw a group meeting up in New York, in Central Park, for a workout together they’d never met before. It was using early signs of community that we had never seen in the original Ladder business. That was unbelievably exciting, it was like holy cow moment for the whole team. That was enough for us to feel pretty confident that there was an exciting business to be built here. So in early March, we locked in the plan to build Ladder Teams from scratch.

Sean (38:57):
Okay, so Ladder, the company, goes from the one to one, coach to consumer app to piloting what eventually becomes Ladder Teams. And that’s connecting coaches in a one to many environment, but also connecting the consumers to each other. So they can interact around a common theme, in this case, a program workout. And that was essentially, the shift.

Sean (39:26):
As I talk about many, many times, one of the most important things in business is timing, and sometimes timing is way out of your control. So you pilot this, you improve a little bit of the functionality, the team starts to get excited with the feedback. Then a little thing known as COVID hits everybody right in the reality check. Then it forces another shift. But in this case, your research and your timing might have worked to the benefit because all the gyms then shut down, and people were still looking for two very important things: how to do fitness routines, as well as how to connect with people, in that process. Both things were kind of pulled away from us.

Sean (40:15):
So share a little bit about the impact that that had right as you’re launching. Right as you’re launching the new Ladder Teams March 2020, the world shuts down. What do you do?

Greg (40:29):
Yeah, we locked in the strategy, and we did those betas before COVID. There were whisperings of COVID. But it wasn’t mainstream. It wasn’t part of the conversation in January, February. And our target user that we were building the product for was somebody who was going to the gym, it was somebody who was already into fitness, knew what quality looked like, knew what good coaching looked like. This is someone that had access to a full basket of equipment.

Greg (40:59):
We had our first really deep planning session with this new team after the last couple folks joined on Sunday, March 15th, of 2020. That next Monday, literally the next day, it felt like the world changed overnight, and we closed the office, and we sent everyone home to work. So we spent 100 days literally 100 exactly from that moment, building Ladder Teams in a fully remote manner. We launched this new business, this new app, the last week of June in 2020. So literally the middle of COVID.

Greg (41:39):
And as we were building, we knew pretty quickly that our consumer was not going to be in a gym anytime soon, and that most of these folks are super into fitness, but they never worked at home, not even part of their calculus in terms of their fitness routine, which meant that they didn’t have weights or equipment in their house. We had to navigate this. So certainly tailwinds in terms of an open mindedness and the consumer looking for new things at that moment in time and certainly coaches who were looking for partners because their worlds were flipped upside down.

Greg (42:12):
But there were a bunch of challenges that we had to navigate to make sure that we could thrive and survive and win in a COVID lockdown world and we did a couple things that looking back definitely helped in that moment. I mean the first was finding the right partners and coaches and we talked about earlier how important it was to have alignment between the coach and our business and our team and the first business is independent contractors very hard to control. As new business we partner with coaches who all have equity in the company, are super aligned, are in our Slack working with our team. So a lot more control and alignment on the experience that we were delivering together.

Greg (42:57):
But what we were looking for in addition to being phenomenal structured workout programmers and known for their craft and community builders we looked for adaptability just like we would look for in a teammate. We had engineering and product and marketing, and we ask ourselves fitness coach be effective across different workout environments – for the first time ever, could they keep a large group of people excited, could they deliver challenging workouts for someone at home with no or little equipment. We just went deep into trying to understand how these coaches thought to really make sure that this is someone that can bob and weave at this stage as a starter but also in a new world that we were living in, different for them as a professional than they did pre COVID. So that definitely helped. The second thing we did-

Sean (43:48):
So more scrutiny on which coaches were in your network and selection, as well as empowering them and enforcing them and investing in them.

Greg (44:00):
No question, and thinking about them as team members, working with them. We would have investors ask as well what happens if a coach leaves? And I would ask well, what happens if my head of engineering leaves? If head of engineering leaves, that’s a bigger problem. I need to manage the team in a way that keeps people excited, and they’re fired up to be what do whatever we’re doing, I think about coaches the exact same way. They’re on the team, I need to be transparent with them that clear goals, make sure they’re getting recognition for wins, and keep them motivated financially and with equity to be aligned.

Greg (44:35):
So that was new to most of these coaches, and definitely helped us get meetings with folks that we probably should not have had meetings with. A lot higher profile in the coaching busines that we’re not going to see because we were pitching on PowerPoint pages, at that point.

Greg (44:51):
But a couple other things we did at that moment is we thought about how do we create content as a business, and when we launch a new coach or new program on the platform, we fly the coach to Austin, and we have a high performance training facility on the first floor of our office. We shoot about 1000 individual movement videos very different than most fitness companies are asked where they shoot a piece of content front to back, we share them as individual movements, because this is workout programming, those movements are tied together by a coach who knows how to tie them together. Our product, decouples video and audio in terms of how we think about content creation.

Greg (45:32):
So the movement demonstrations, the coach on your phone doing the exercise that you’re supposed to be doing, those videos are shot one time, and they’re shot in our gym, it’s very controlled and high quality and you get a final production. But the audio is recorded every week, over the top in our coach software. So you have the coach in front of you in high production quality media, and then you’ve got them in your ear coaching, motivating, tying to current events, storytelling, and that kind of makes the magic of the experience. What we did with COVID when we watch the whole world shifting to at home, we had them filming all day, literally working out for 12 hours in one single session to shoot all bodyweight, all equipment.

Greg (46:24):
So we just had everything we had this arsenal of content that we could program no matter where somebody was, that was like our defense mechanism against COVID from a content perspective. That was helpful that’s become core to how we build product and run the business.

Greg (46:41):
Now the last thing we did, which is a little bit more unique is we locked down a partnership with Rob Gronkowski and his family who owns a fitness equipment distribution business up in Boston, we put some cash down basically begging him, and they agreed to secure a bunch of kettlebells, bunch of dumbbells, a bunch of bands, which you couldn’t get anywhere in the world at that point. Everything was out of stock. I don’t know you remember this, but like-

Sean (47:11):
Oh, yeah, still is out of stock.

Greg (47:15):
We stood up this jaggy Shopify page to sell equipment, that have our logo on the screen. We essentially had all of this equipment that was out of stock everywhere that people were looking desperately for. We offered it to people who started a free trial in our app. So it was a pretty clever solution to solve their problem on equipment, but pull them in to the app when they might not have been open yet to using an app from a workout perspective. It’s funny, thinking back on that moment now, but it just became another thing we had to do to get this off the ground.

Sean (47:54):
Yeah, I mean, in the middle of launch, you have a major supply chain impact on multiple levels, and you have to focus on creating the new experience. So the second step of investing in your studio and bringing the coaches in is super important, but if your end users didn’t have equipment to do the program, it kind of fell flat. So you had to make multiple adjustments. Like all of us did, but that’s your guys’s personal journey story. It’s quite amazing. Okay, so Teams is out, getting subscribers, and then there’s a little story wanted to share about 20 women who connected within a Team. What happened?

Greg (48:41):
Yeah, this was like a month and a half ago, maybe two months ago. But one of our programs, called Body and Bell coached by Lauren Kanski. She’s actually the coach that I mentioned earlier on the beta program. So she’s been with us through this whole thing. She’s been a phenomenal partner. But we had this group of women who met each other in the app in this program, and they were very quickly becoming best friends, and we give you ways to communicate and share experiences with each other in the app.

Greg (49:12):
So in COVID, when everyone is stuck in their home, they found others who were passionate about fitness, going through the same thing, working with the same coach. And they found comfort and support in each other. We heard rumblings in like some of the chat rooms that some group was coordinating some trip to Austin, and we learned that this group of 20 women were trying to figure out how to get together when the world opened up in Texas, in Austin, and this group came to Austin, they booked a big Airbnb house, they all flew in from around the country and two people from outside of the country to meet each other for the first time. They trained together, they did a bunch of stuff around Austin, they did a bunch of dinners together. And we got to watch them come to Ladder, and spend some time with them and work out in our gym. It was an amazing, amazing thing that you can see the passion, you can see these people were really, really close friends. They literally just met that morning or that night for the first time.

Greg (50:23):
We watched that and just thought, “Wow, there’s something here,” like this is pretty incredible. We didn’t force this, we didn’t create this. We didn’t build this trip, they just organized themselves. And they thought it was important enough to go spend a whole bunch of money to meet each other. We’ve had those experience play out over and over again in other programs in our app, and that’s been just really, really exciting and rewarding to see and to hear those stories.

Sean (50:48):
Talk about a network effect. That’s a pretty awesome one. Okay. So what’s next, Greg? What’s the vision a Ladder? Where do you want to take this thing?

Greg (50:58):
Yeah, so we just closed a seed plus round which was extremely helpful, gives us some capital to support growth to build out the team in some key areas. We’ve got a ton of exciting things coming from the product perspective. But we’re still in a phase right now. I’m not sure this will ever change where we’re maniacally focused on our members, we’re learning from them every day, I’m talking to them on the phone. We’re surveying them, we’re watching what they’re doing and trying to figure out, how do we turn their problems, their challenges into an even better experience. We’re listening very, very closely, and the whole team kind of has that ethos.

Greg (51:44):
As part of that, we’re trying to build, especially seeing these stories and seeing people meeting together in real life, we think we can build the strongest, most authentic community of people who share a passion for fitness, and want to support each other. That’s kind of our guiding light, so excited about where we are and hiring some smart new folks to join the team and got some exciting things coming in the very near future.

Sean (52:14):
And that’s how you find opportunity in a crisis right there. So that is super, super cool. Best of luck to you and the team and your coaches as well as your users. If you want to find a way to get a little healthier physically as well as mentally by connecting with people in these challenging times. Greg, how do people get in touch? How do they find you?

Greg (52:39):
Yep, you can check us out at our website, joinladder, just as it sounds, or you can find us in the Apple App Store, just search Ladder. Yeah, we give you a seven day completely free trial, we don’t collect your credit card, which is pretty rare in this space, and you get to explore all our programs, all of our coaches and communities to find the best match for you. So come check it out.

Sean (53:00):
Awesome. Well thank you for sharing your story of how you’ve launched and relaunched the company and ever striving for product fit. I think it’s an amazing story. We’ll be tracking your progress and rooting for you and the team. And I really appreciate you giving some time back to the Salesforce community and lessons learned. So thank you.

Sean (53:25):
In our next episode, we are going to interview a very experienced Chief Product officer at another Austin company. But we’ll be going back to the AppExchange and seeing what they’re doing. That’s super cool in the pricing space. So I look forward to that next episode.

Sean (53:44):
Greg, thank you again. Stefanie, thank you for being our host on this and we hope you enjoyed this latest episode of How I Launched This.