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ZERO TO ONE 🌱

Unfiltered: Launching Sidebar

Recently, I wrote about a ragtag bunch of ex-Facebook leaders who drove Sidebar’s journey from zero to one. Today, I’d like to share the behind-the-scenes content from that piece. Why? Because I am a business nerd, and I lap this stuff up. And if I know you well enough, you likely will too.

The team at Sidebar worked around the clock like scientists with a chip on their shoulders in the lead-up to their launch, so there are some real gems of wisdom here.

Caveat: This piece is long. So my suggestion for you is: a) to read every single word of it (of course, this is best), or b) pick and choose the areas that are most interesting to you. That’s it for now, though. Enjoy the piece!

Lexy Franklin, Founder & CEO at Sidebar

Lexy Franklin is the founder and CEO of Sidebar, a leadership program with expertly matched peer groups, goal tracking, messaging, and facilitated sessions customized to each person. Lexy brings over a decade of product innovation experience with leadership roles at Meta, Striiv, and Booyah, Inc. He holds a bachelor’s degree from Stanford University.

What made you want to start Sidebar?

When I was at Facebook, I was surrounded by the smartest people I'd ever met. I wanted the opportunity to come together across disciplines and learn from each other in a concrete way, but everyone was so busy. That type of peer collaboration on the craft of work was harder to find, and that was before the pandemic. After the pandemic, finding this type of peer connection on how to do our jobs better became 10x harder. If this wasn't happening at Facebook—which I thought was the best executing company I'd ever been part of—then the opportunity was there for all companies.

What was the initial idea, and how did you validate it?

I'm a big fan of the book ‘Sprint,’ and I really believe in running sprints to test ideas. Sidebar was actually the eighth idea I was working on over a couple of years while trying to find what made sense next. The origin of Sidebar came from exploring positivity. I was working as an EIR at Foundation Capital, trying to find something that was atomic and fundamentally human.

They asked what was atomic to me, and I said I'm a positive person and I have an amazing mom. They suggested I explore that: How would I build something that gives people an experience similar to what I experienced with my mom? She was my superpower, the person I went to for tricky work challenges. She'd be an authentic sounding board, usually to tell me I had messed something up and needed to fix it.

I'd feel bad about telling them what to do instead of just being positive, but they'd say, ‘That was amazing, I did that the next day, and it really worked.’ This kept happening over and over. The bright spot wasn't the positivity idea itself, but when I would give them my work perspective. That's how Sidebar was born from testing this other idea.

How did you choose the founding team?

We were so lucky to have wonderful people on the founding team. Everyone is just an honor to work with. I always wanted to work with people where you'd get excited to see them every day. They're smart, they think in diverse and brilliant ways, they're good at getting things done, and everyone's belief in the mission is really clear.

It's an incredible collection of people who do exceptional work and hold the bar high. We push each other to grow, learn, and be better, and we're laser-focused on building something that matters in the world.

I was trying to find people who were comfortable very early on—comfortable getting stuff done, taking on undefined spaces and defining them, and working together. The metric I used was: ‘Would I get on a plane and sit in the middle seat to try to bring this person on the team?’ For every early employee, I felt that very strongly, and we still use that metric.

What was something that crushed it in the early stages?

Two things we did well. First, we charged from day one. We measured the value of the product by whether people would pay for it. I think the rubber hits the road when people are willing to pay for something. From the very beginning, we knew there was a business associated with it. We used to Venmo people, and they would pay us, then we'd Venmo the money back because it was too early and there wasn't really a product there, but that was in our core ethos.

Second, we thought about how to build it from a product systems perspective early on. We had tremendous help from brilliant team members who educated us on the right approach. We felt this was a system where we could match people effectively, communicate with them effectively, and connect them on calls in the right way. We were very diligent about what needed to be systematized so this could grow quickly.

What's something you wish you knew then that you know now?

One of the gifts of founding companies is that you learn things every day, where you think. ‘If I did this again, I would do that differently.’ First, having a cap table with a diverse set of skill sets is crucial because ultimately, you're always hiring. You're trying to hire the best possible people, and sometimes those hires are in areas where your network isn't as deep. Having different people on the cap table who can champion different areas of expertise. Having them be able to jump in and say, ‘this is a really good go-to-market person’ or ‘this is an excellent designer’ is super helpful. This is counterintuitive to the prevailing wisdom about keeping your cap table small.

Second, in small company life, speed is everything—how you execute, how fast you get stuff done. Without the infrastructure of a larger company, you really have to work at it. I'm a speed-oriented person, and one of the things we think about all the time is ‘How do we do this today versus three days from now?’

Third, always think about who on the team can own something. Who can take something so you know it's going to get done efficiently and on time? I didn't understand this as deeply earlier in my career, but now, when you see people executing well and being owners, it's incredibly impactful. It's changed my philosophy a lot.

What's something that bombed in the early days?

So many things. If you're good at products, you're probably only right 10 to 15% of the time. One thing we tried early on was a much less structured curriculum for Sidebar. It was much more focused on support, which we think is important, but many of the goals, functionality, and work focus weren't built in. We got overwhelming feedback that while support was necessary, without those other qualities, it wasn't as impactful as it could be.

Another example is that we've updated how we match people quite often. Many aspects of matching are counterintuitive. If you match people just on job title, it's cool that it's two VPs meeting each other, but those VPs could be working in completely different roles doing completely different things. The context of the work you're doing day-to-day is much more nuanced than your job title. Incorporating that context into the types of problems you're trying to solve has made our groups substantially better.

💡 Note: I am leading a webinar with Sidebar on their new product, Superinterviews, to help people crush job interviews. Sign up here.

What was the initial go-to-market like?

The initial go-to-market was really focused on friends of friends, trying to figure out the bright spot. There's a great article from Paul Graham about how to get your first set of users—it's completely unscalable. We had a brilliant team member, Maddie, who bootstrapped, trying to figure out how to get those first hundred people just to test and iterate.

We tested with about a core group of a hundred members in Sidebar for over a year, just iterating and playing with it before we turned on any growth mechanisms. We wanted to make sure this was super valuable. Then we'd add some more people to make sure we weren't optimizing for too small a number.

When we started to grow quickly, we had brilliant people help us, from the early team to investors and advisors. But when we started turning on the different growth mechanisms, we knew we had solved a lot of the core product problems. We had all that data showing this is sticky and works—that was something we cared about early on.

Founding Team, Jeremy Barton, Asher King & Samantha Bergeron

Jeremy, Asher, Samantha are all early hires at Sidebar, but all come from very varied backgrounds. Jeremy is a former Facebook product builder who worked alongside Lexy for many years. Asher had a previous life as a professional surfer and Samantha, who has a consumer behavior research background, began as a consultant for Sidebar before joining full-time. These three will help give further color to the story of Sidebar’s early days.

What was your exact role in the zero-to-one stage?

Jeremy: My role was head of product, specifically tasked with building something that people really loved and that we felt had high conviction we had market fit with. On the founding team, everybody wears a bunch of different hats, but ultimately, the whole company was aligned on building something we were highly confident in, which we believed had market fit.

Asher: I don't know where to begin. I think the only thing I haven't done at Sidebar is contribute to our codebase, and that's just because we wouldn't want that anywhere. Early on, it was a lot of ideation and early product work. We actually started as a one-on-one coaching service—like a scrappy 15-minute coaching service—and I was doing all the coaching at that point. When we evolved to the group model, I facilitated all of our groups for the first 12 to 18 months as a company.

I've done early branding and positioning. My background is marketing, both on the performance marketing side and on the brand side. Then, about a couple of summers ago, as we started to know that there was a ‘there there,’ I transitioned to membership, which is our approach to sales and all the pieces of the go-to-market puzzle.

Samantha: It's a little bit of a complicated question because I started as a consultant. I think there were three employees when I joined as a consultant. Lexi and I were connected through a colleague of mine. My background is in consulting and I do consumer behavior research, really understanding consumers and what drives and motivates them.

How did you go about researching the opportunity?

Samantha: It's interesting because for a startup, it's very different, very much rolling up your sleeves and just getting in there. We started with this big piece of foundational research because, as a consultant, we put together this beautiful battery of knowledge. We started with a pretty deep foundation of who this customer is.

When I joined full-time, we started integrating the customer into every decision. Whether that's ‘we know this about them, so this is the right decision,’ or ‘we're going to get input on this idea before we build,’—it really created the cycle where we don't make anything that we can't link to a customer need. If we can't find the customer need, we won't build it.

It's tough to be that disciplined, but it's critical because otherwise you're building things no one cares about. We try to put them at the center. We do lots of qualitative interviews; one-on-one conversations about what they think, how their experience is going, what's working, what's not. We do that at every stage. We talk to members who chose not to join, members who have recently joined, and members who've been with us a long time. We do exit interviews with anybody who's left.

On any given product project, we'll do focused interviews to get feedback on designs and usage. Our access to data and the volume of data we have has grown exponentially over the past two years, so we're getting smarter about leveraging the data and tying that back to our decisions. It's gone from largely qualitative in the beginning—because we didn't have any data—to a beautiful symmetry and mix of qual and quant.

Recently, we've been able to start drilling down on who is our best customer, what that looks like, and what indicates somebody is going to retain. That will enable us to really double down and super focus on them.

What was the deciding factor that made you lean towards groups?

Jeremy: Ultimately, it came down to value for users. This breaks down to a couple of things: First, with one-to-one coaching with professionals, it's extremely valuable, but so much depends on the coach and their coaching style. The benefits of peer groups are that the conversations are much more tangible because people are discussing their shared projects in real time. The group is learning together, so the conversations are much more tangible and tactical, which creates more value.

Second, you get the group brain. Instead of having a one-on-one coach with one brain, you get five to nine other brains giving perspective on your problems. It's social and fun too. You feel more supported, like you have a little community around your work, and you don't feel as lonely.

We also did tons of research and saw that peer groups are something humans have been using to create community, solve problems, and have accountability for so long. Peer groups are just so valuable, and we saw that in the market as well.

What did the go-to-market look like?

Asher: Our first hundred members were all of our friends. It was so interesting because even then, it was awkward to ask them to pay, but we had to have the forcing function for payment to know that it wasn't just somebody doing us a favor. In the early testing, even before the 0.001 stage, we'd have them test the product, then they would decide if they wanted to move forward. We would take their payment and then just refund them because you need to see that pressure test if there was a real desire for the product.

Once, that was probably 50 to 100 people; it was a lot of asking them who the best folks they knew were. It was way more hand-to-hand combat than even referrals—we would get on the phone with people, talk about what their experience was, who else they thought would be interested, and then reach out to them or have them get people in. It was hard and really vulnerable because I've never been comfortable asking anyone for anything ever, and it was all day, every day, just asking people for things.

We were thinking about what other channels we could explore. There was a lot that didn't work. I've worked on paid ads for years, especially in performance marketing—paid search, paid social—those things didn't work great. We tested it, and it just didn't seem like the right tool for the job.

We went to our investors to see who they had. We went all over the map and got us to about 200. At that point, it was clearly not going to get us to the next stage, and we needed to get more people into Sidebar to increase our matching pool. The whole experience gets better with each incremental high-calibre person that comes in, as we needed that network effect.

That's when we started looking at newsletters and podcasts, with the idea that people reading these are there to consume content and sharpen their skillset. The intent would be better. That was an excellent source for us, especially Lenny's newsletter—finding people who believe in the idea, who say that having this peer network has been a big deal in their life. When we looked for partnerships with people who didn't believe in Sidebar, you can't fake the funk. If there was that misalignment, it would show up and wouldn't bring the people we were looking for.

The best way for us to build trust and acquire that first group of believers was to find other people who believed in Sidebar, who had trust with their audience. That was the first principle of why newsletters as a channel worked—there were people who had cultivated trust with the people they talked to. If they believed in Sidebar, we believed in them. The authenticity shines through, which is essential for end customer acquisition.

What was the one thing you really nailed?

Jeremy: I'm going to cheat and say two things. First, we took a research-focused approach to our work. We tried to research first before just building. We wanted to make sure we found that nail and understood it, versus being a hammer looking for a nail.

Second, we had a massive focus on constant user feedback to understand market fit and ultimately retention. Retention is a proxy for the value we're able to deliver to members and how well we're solving their problem. We followed the First Round Capital published playbook from the founder of Reportive, who did this whole product-market fit using the ‘very disappointed’ survey approach. We took that approach and tried to follow the playbook to a tee.

Samantha: At the risk of sounding immodest or repeating myself, I think the best thing we've done is put the customer at the center of the build. We made this decision very early on, and it was very innovative of Lexy. It's unusual to bring a researcher in at the beginning. It's usually something you do much farther along when you have something to research and get feedback on.

He had had a great experience with research in his earlier career and truly believes in it. So he brought me on very early, and putting the customer at the center has allowed us to build a product that we would have had a very different product otherwise, and we would be far less successful because we would have just made a bunch of stabs. Because we're building with our customers and keeping them at the center of the product, it's allowed us to build in a really smart way.

What's something that bombed?

Jeremy: Something that really bombed early for us was how to think about describing Sidebar and how we could grow the initial member base to get feedback on it. We constantly set goals for ourselves that were way too ambitious and unrealistic.

We had a ton of learning around that initial balance—we weren't public, but we still needed to have members and to grow so we could get feedback on the product and iterate and make it better. Our approach to that was probably incorrect at the get-go. We thought it was going to be a lot easier to grow and get new members than it actually was.

Samantha: I think one of our biggest mistakes was around the holidays. We saw in our first year that attendance over the holidays was abysmal. Attendance is everything—people don't show up to groups, and everything falls apart. We tried all these things. We asked groups to vote on whether they wanted to have meetings over the holidays or not, moved things around, and it was abysmal. Scores were terrible, and everyone was upset.

So the following year, we canceled regular meetings during the holidays entirely. No meetings from Thanksgiving to the end of the year. We put all this optional programming in so you could attend a Sidebar meeting every day, but your regular meetings didn't happen. We figured it was the best of both worlds, you're not required to go to meetings, you have flexibility.

But it absolutely bombed. We haven't done anything else that has made members that mad. They felt like we were taking away their opportunity to meet with each other. They felt like they were missing out on the value. They felt like they weren't as bonded. I still don't know the right answer, but I know that it's not to cancel things.

How well did the launch go out of 0 to 10? What would have made it a 10?

Jeremy: We had two launches that both went pretty well. The first was when we launched our wait list in early June of 2023. We shifted the frame and opened up an ability for people to join the waitlist and express interest in Sidebar in a lighter-weight way. I thought that went really well—we executed a good plan that helped change our momentum with go-to-market.

Our official launch was in the fall of last year, and I thought that went well, too. I'd rate both of those about eight out of 10.

For the official launch in the fall, it would have been ideal if we had expected more coverage of the importance of this problem and the approach we're taking to solve it. We got tremendous engagement from our member base at the launch, which was super positive. But we expected to see more engagement around the problem space—work is such an important part of all our lives, the challenges we all face with it, and the importance of people feeling supported.

Tell me about the most difficult time you had in the launch?

Asher: I think a challenging moment was when we were deciding if it was or was not the right time to grow. 100 to 150 people were using the service, which is such a small sample size, especially with something we expect people to use for three years, five years, ten years. A bunch of people who have been using this for three to six months—it's a tiny sample size to make life-altering decisions from.

Using the best interpretation of your data with all the quant and qual signals at hand, you have to go face-to-face with imposter syndrome. There's no chance you're going to have enough information to say you have 100% conviction this is going to work, but you also can't sit still. It's like "here's the stuff we notice, here's what the numbers say, here's how they interface with each other." Deciding to press the button, you have to come face to face with a lot of emotions that I may have been told about before, but facing them in practice was different from theory.

A few times when people churned in the early days, I knew everyone personally. When somebody churned from the service, it's tough to separate yourself from the reason—is it the product or is it us? You forge intense relationships with these people. The first 10 people who churned, it was like going through a first breakup 10 times, because I was on the facilitation side at the time. That was challenging.

_{*Note: The screenshot below is from Sidebar’s new Superinterviews product. It’s a tool that helps you crush job interviews with ease.}

Samantha: I think one mistake we've made a couple of times and that we're still getting better at is we, as an organization, assume everybody—our members—are coming along with us. We'll assume we have the product and there's a program tab with all the necessary information, so everybody knows about the program. They know exactly what's coming up next and they can look at their last meeting.

It's just not the case at all. They don't even know the program tab is there. We sort of miss that education stuff. We've had a couple of examples where we're trying to establish rigor around when we launch something—we have to tell everybody more than once, we have to teach them to use it, we have to bring them back to it regularly. Even though it's something we know they want and need, if they don't know it's there, it doesn't get used. We're getting better, but we've got a ways to go on the education piece and giving that enough time and space that it really works.

What is a hypothesis you had that has changed over time?

Samantha: My absolute favorite example! When we first started the business, we were treating it like—I have this analogy I love to use—if you think about a gym, we really started as a gym. You pay monthly, you go, people are nice to you, you don't go, it's fine. But it's a lovely place to be if you choose to go.

We did so much research and got so much feedback, and we learned that what members come to us for is rigor and commitment. So we shifted the whole business model to be much more around commitment. Attendance is expected and required, and lack of attendance will result in you changing groups. We try to push our members to achieve their goals.

A very recent one is that we just assumed that members who nominate other members to join the community were our best members—high scores, high attendance, love Sidebar so much they tell others. Not the case at all. People who nominate have a wide variety of backgrounds, levels of engagement in the product, and lengths of time in the product—it's all over the place. We're doing projects now to understand what that theme is and what drives some people to nominate and others not to.

You can follow Lexy Franklin and check out Sidebar if you are looking to build and grow your network of peers, and Superinterviews to land your dream job.

BRAIN FOOD 🧠 

TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️ 

Every week, we highlight tools we actually use inside our business and give them an honest review. Today we are highlighting Taplio—the tool I use to grow and manage my social media and online presence.

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