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📢 New Media, Legacy Media & How To Do Founder PR. An interview with Emilie Gerber, Founder & Principal at Six Eastern.
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HOUSEKEEPING 📨

I found a guy who launched an app that I absolutely love. So much so, I tried to buy it from him (kinda). The app, brainrot, helps you break phone addiction. When I am daydreaming about problems I would happily dedicate my life to, destroying social media addiction would be very high on the list.

Other things that would rank highly: cultured meat, robotics, climate tech, and longevity, but for dogs. But, I have my hands full—happily, I might add—with Athyna, and this very newsletter for now. But a man can dream. Anyway, nothing more to add. Enjoy today’s post!

ZERO TO ONE 🌱 

How Sidebar Went From 0 → 1

Sidebar, a company whose mission is to connect leaders and catalyze their extraordinary success, is running rampant through startup circles. Founders, executives and product leaders all across the US, Europe and APAC have been using it as their secret weapon to move their careers forward. I would know, I am one of them.

But they didn’t start here. Every successful startup story usually begins with coughs and splutters. It starts with many failures and near-death experiences and is followed by many more near-death experiences and failures.

Today’s story is a group of ragtag ex-Facebookers cum Metanites, led by their supreme leader Lexy Franklin, who decided to take on the leadership coaching space, and seem to be winning. To understand the story of Sidebar, and how they went from zero to one, I sat down and spoke with the founder, Lexy, three founding members, Asher, JB and Samantha and also two happy leaders who use Sidebar to supercharge their careers, Ananda & Ha. Some of you may remember Ananda from our deep dive last year. We met at Sidebar.

Rapid experimentation

Our story starts in late 2020, with future founder, Lexy, working as an EIR (Entrepreneur in Residence) with Silicon Valley’s Foundation Capital.

This was where Lexy was able to put on his mad scientist hat and test a whole bunch of crazy ideas, with the aim of finding what he wanted to build in this next stage of his career. He tested and experimented with no fewer than six ideas before landing on coaching and Sidebar. Check them out here.

Interesting right. After speaking with Lexy, he told me that the idea that had the most legs outside of Sidebar was the idea to dating app he started with his buddy, Jeff Kanter. Jeff went on to raise capital for the idea, which turned into Castro Labs.

It wasn’t until he stumbled upon the “Soul Cycle for your brain” that the idea of helping people grow in their careers came to the fore. The pull was so strong that Lexy decided it was time to transition to the next phase of this idea.

Market validation

To truly validate a market, you usually need to know what the market is. Therein lies Sidebar’s problem. What was their market?

Whether it was the Chief model of private network and leadership development, BNI’s worldwide referral pushing parade or the global executive coaching market, said to be valued at approximately $9.3 billion as of 2024, they knew there was a market. Take a look at some of the data below. Revenue growth, tick. Positive impact on productivity, satisfaction and more, tick. And the final thing, companies are willing to pay to develop their leaders.

Armed with these insights, Lexy was able to go and raise a $13.5 million seed round from Foundation Capital, Scribble Ventures, Pinterest co-founder Evan Sharp and several other helpful angels. Next stage: hiring.

Employee #1: Asher King

No true zero-to-one story is complete without a deep dive into the early team, and ideally, the founding team. Lucky for you today that Sidebar’s first foot-soldier still wears Sidebar on his sleeve. Sidebar’s first hire is the San Diegan, ex-pro surfing and all-around ball of passion, Asher King.

Asher joined Sidebar after a coffee catch-up with Lexy on a visit to San Diego. Lexy knew he needed to talk to the best coaches, and Asher used to be Lexy’s surf coach. “I joined Sidebar before it was a thing. It was only really a small glimmer in Lexy’s eye at the time.” And like all great zero-to-one employees, Asher wore many hats. He built the brand, ran the first set of hiring, taught the first months of the program, and now finally “leads membership”—aka sales—for the team. “The only thing I haven’t done at Sidebar is contribute to our code base,” Asher told me.

For me, though, meeting with Asher didn’t really just fill me in on the blind spots I had within my story; it told me how Sidebar really thinks about Sidebar. Asher, by definition, is Sidebar. And he knows he was meant to be doing this. “I just want this to exist in the world so badly. I absolutely could not picture myself working on anything else.”

So much money goes towards companies adding negative value to the world. And to companies that are not mission-first or people-centric. Sidebar is not one of those stories.

The story of Asher is the story of Sidebar’s team, its founder, you, me, and all of Sidebar’s members. If you are reading, I know you are ambitious. I know you want to improve. I know you want to leave a positive dent in the world. This is why Asher does it. We are all Asher. And there is a little bit of Sidebar in all of us.

Early hiring: Band camp, Facebook Alum & building Messenger Kids

So if Asher was the first lemming to dive headfirst off the Sidebar cliff, who was next? Well, first, we need to take a walk down memory lane.

The year is 1999, Blink 182 had just topped the chart with ‘All The Small Things,’ Tony Hawk Skater was eviscerating thumbprints all across the world, and Lexy Franklin and Jeremy Barton are becoming fast friends at Yosemite Band Camp.

The two 15-year-old, snotty-nosed, pre-pubescents were totally unawares that the friendship they were forming would one day take them through college, a blitzscaling mega-unicorn, and ultimately working together at Sidebar. "I've known Lexi for about 20 years... We've always just stayed close, talking about big ideas and problems that impact a lot of people,” Jeremy ‘JB’ Barton said, reflecting. “I recruited Lexy to Facebook actually. He joined because of me.”

_{*Lexy and JB corrected me at the very last minute—they were 19, it was 2005, and it was Lake Tahoe Camp.}

Once you start to navigate your way around Sidebar, you do begin to notice a couple of themes: firstly, everyone loves working together, and secondly, everybody is from Facebook.

Not only had this team worked together before, but they had also worked at one of the most impressive organisations in the four-billion-year history of planet Earth. "We learned so many different things from Facebook. Understand, identify, execute. Moving fast. The speed and efficiency of things. That is what was important.” I actually spoke at length with Lexy about how he thinks about speed. He told me that “We never go to bed on problems.” What he meant was that they never go to bed with decisions hanging over their heads. They have a meeting, decide, and make progress. A clear principle taken from the team that moved fast and broke things.

In the very early stages, this team was bonded, they aligned, and every member was trained in an incredible ecosystem. And they were sharp. Like an archer’s bow, pulled all the way back to full extension, just waiting to be pointed at the right problem.

One person who was critical to the success of Sidebar in the earliest days was Samantha Bergeron. Samantha started initially as a consultant to Sidebar, but shortly after came on to be a member of the founding team. Samantha was in charge of behavioural research. “At the beginning, I was focused on the basics: who is Sidebar right for, why will they join, what do we need to provide for them, how do we win.”

So the early team was set. An eclectic but talented mix of characters from in and around Lexy’s orbit. What stood out most, though, was the bond this group had together. "I always wanted to work with people where you kind of fell over because you were so excited to see them every day,” Lexy told me on one of our calls.

Behavioural research & ‘Project Sunshine’

What I found most interesting with the Sidebar zero to one story was how much thought and care—and financial investment for that matter—went into the launch. From the very first days, Lexy and the team employed Samantha not just to have a few user interviews but to run a behavioural research program. An example of this is something Sidebar called ‘Project Sunshine.’ I have access to the 34-page document outlining the systematic approach to testing.

And it was effectively to run small group coaching for two cohorts: founders and product managers—their initial ICPs. There were 16 founders and 16 product managers in the initial testing group. Here are some of the initial discussions from their research around the two.

The eventual learnings were that group learning and support provided more value than one-to-one coaching, matching was better suited to be around problems than geographical or job title/department, and the vibe really mattered.

Another thing they found was that structure and programming were key. "We really started as we were a gym... We did so much research and got so much feedback and we really learned that what members come to us for is rigor and commitment,” Samantha would say. Something I found pretty interesting was that: “1:1s complicate the group experience as they don’t directly complement each other. There’s not a clear correlation between the two. They also add another layer of scheduling challenges,” the research concluded. One-to-one seemed valuable, but not helpful enough to be part of the product in the long term.

Two other elements worth highlighting are that matching facilitation bubbled right to the surface in order of what was important to people. The initial group in Project Sunshine ranked matching a 2/5. The takeaway being that, “Groups only work when members have shared personal and professional experience and everyone feels all members are as good or better than them.” As good or better than, is by definition impossible, but the key for Sidebar really was making sure people didn’t always feel like the smartest person in the room.

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

And the other thing that was key was that the group’s facilitator was key to the success. This is something that Sidebar, at least in my experience, nailed from the start. My facilitators have been Megan, Chris and Maddie so far in my groups. Megan was in leadership development at Meta for 8 years, Chris was a facilitator at Shopify, and Maddie was talent and org dev at Eventbrite for nearly a decade. Bonkers.

Overall, this was the definition of going through a process to find a product market. Samantha put it best herself: "Putting the customer at the centre... has allowed us to build in an ingenious way.”

MVP → Beta launch → Public launch

One great way to validate product market fit is to see if people are willing to pay for your product or service. "The first thing we did really well was we charged from day one, so we actually measured the value of the product, whether people would pay or not,” Lexy would say. It’s “where the rubber meets the road.” So now that they’d passed their MVP stage, it was time for true beta users. I asked Samantha what they looked like.

But how do you actually go out and find those people? Well, according to Asher, the initial go-to-market was simple: "Our first hundred members were like all of our friends ... it was such a core group that it was really awkward to ask them to pay but we had to have the forcing function for payment to know that it wasn't just somebody kind of doing us a favor.” Like most good startups, it started with friends and family.

But armed with a boatload of VC money and ambitious plans, the team needed to find the next growth lever. They turned to “hand-to-hand combat by referral,” says Asher. “We'd basically get on the phone with people and talk about what their experience was, who else they thought was gonna be, somebody that would be interested in this, and then who fit the archetype. We then would go reach out to them or have them and get them in.” For those who aren’t keeping count, here is where we are at.

To continue to gain momentum, though, they needed an acquisition source that they could turn on or off like a tap. And being disciples of the God of paid acquisition, Mark Zuckerberg, they did what all good VC-backed companies did: they ran Meta Ads, unfortunately, unsuccessfully for now.

Asher believed that you were not really able to leverage trust in any meaningful way. And for something like Sidebar where people are going to invest not only money, but their time, it was a really important factor. So they pivoted to channels with higher signal and where they could leverage trust and reach better audiences: podcasts and newsletters.

And that brings us to today. Sidebar’s GTM leans heavily into leveraging great audiences in tech. This newsletter, which you can read right now, is an example. But you may have also seen them in Lenny’s Newsletter, Bay Area Times (my startup Athyna’s largest investor), Strategy Breakdowns and more. They are also in some of the largest podcasts in the world.

Sidebar didn’t share overall membership numbers with me, but up until very recently, they had a wait list of over 35,000 people.

And they boast members from Microsoft, Nike, Meta (duh’), Instacart, New York Times and loads more. So it’s safe to say that the strategy seems to be working.

A retrospective playbook

What worked

• Building the All-Star team: The founding team were a mix of players, all with excellent pedigree and with a massive desire to tackle this problem head-on. Most of whom are still passionate Sidebar team members today.

• Charging on day one: One major success was asking people to pay. This helped validate the business model early on, confirming that users found enough value to pay for the service.

• Product thinking: Developing a strong product system early in the process, which was research-led, meant better matching, communication, and connection among members.

• Strong feedback mechanisms: To continuously gauge user satisfaction and refine the product, Sidebar drew used NPS and Disappointment Scores with every member. Something that they still do today.

• Growth via high-quality audiences: Podcasts and newsletters usually have a much higher-quality audience than other channels. Sidebar was able to leverage this in the early days and is still a huge spender on this type of media today.

What bombed

• Less structure: An early version of Sidebar with a less structured curriculum focused on support rather than concrete goals and work-related achievements didn’t work. People wanted structure and accountability.

• Matching on job titles: This proved super ineffective because of the diverse contexts of each role. This led to an improved matching algorithm that considered the specific daily tasks and challenges of every member.

• Meta Ads and expectations: The initial strategies to grow the member base and generate user feedback were overly ambitious and unrealistic, leading to difficulties in scaling up membership effectively.

• Keeping your emotions steady: “In the early days, I knew everyone personally and when they churned, it's very difficult to separate yourself from the reason to churn,” Asher mentioned on a call with me.

Introducing: Superinterviews (and a webinar)

In fun news: Sidebar have just launched a new product, Superinterviews, that helps ambitious job seekers in tech to land their dream roles. I love this stuff, and I love Sidebar, so I’m co-hosting a webinar with founder, Lexy, to jam on what to do when you land your dream interview. Come and join us if that sounds like you.

Summary

So there it is. That, ladies and gentlemen, is how you launch a startup. Or how Sidebar launched their startup anyway. The main takeaway for me here is how much care and effort went into building Sidebar. They didn’t just draw up a lean canvas business model (I love the lean canvas) and hit the ground running. Sidebar was born from meticulous testing, user research, behavioural ‘patternising’ (new word), and love.

And I think the results are showing for themselves. If you are reading this, then you are probably like me, young, ambitious and keen to have a great career you can look on with pride. If that is in fact you, I suggest giving Sidebar a try. Do it for Asher.

Extra reading

• Cybersecured: Vanta’s Zero To One - September, 2024

• Paddle Is Building The Merchant-Of-Record Category - Jan, 2025

• Ted Lasso: The Lasso Way - April, 2025

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 of our business and give them an honest review. Today we are highlighting Paddle—a merchant of record, managing payments, tax and compliance needs—we use their ProfitWell tool.

See the full set of tools we use inside of Athyna & Open Source CEO here.

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