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How Sidebar Went From Zero To One
Launching a startup from scratch is hard. Here is the breakdown of how Sidebar went about it. ⚡️

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HOUSEKEEPING 📨
Today is the first in a new series for us. Today we unveil our Zero to One editions. This week with Sidebar. Next up with have Eucalyptus launching Compound, and many more in the works for the future.
I think these posts will work for two reasons: 1) I am fascinated to write them and 2) I think they’ll be valuable reading. | ![]() Dogson. |
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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 career forward. I would know, for 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 another two happy leaders who use Sidebar to supercharge his career, Ananda & Ha. Some of your 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 EIR (Entrepreneur in Residence) with Silicon Valley’s Foundation Capital.
The fund, led by Steve Vassallo, is a 30-year, 869-investment, tech stalwart of the venture landscape. | ![]() Steve Vassallo. |
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.
What was it? | Why were they building it? | Why did it fail? |
---|---|---|
“The perfect day in Big Sur.” | PDF and audio tour of amazing places to travel to. | Never tested pricing, so unit economics bombed. |
Two-minute phone call app. | “You knew when you got phone call it was only going to be 2-minutes long. So it was a great way to connect with your friends” | “It just didn’t have the long term retention we think we needed.” |
Y-Combinator for brick and mortar stores. | Helping small IRL businesses scale through learnings and ecosystem. | Killed by COVID. |
Dating app competitor to Grindr. | Based on hyper-personalised AI matching. | It didn’t. It got funded. |
“Positive only messaging service.” | You would message the app and it would come back to you with positive comments and ideas. | Was just not viable. No only really wanted it on a daily basis. |
“Soul Cycle for your brain.” | Classes for mental health “recentering.” | People didn’t want it, but they did want a way to get better at their jobs. This was the prelude to Sidebar. |
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 really 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?
Were they 1-on-1 executive coaching? Was it a referral network? Maybe it was actually an accountability club? In the early days it was all and none of those things at the same time. As is common with all ideation stage startups, they knew there was something to validate. | ![]() Executive coaching in sports. |
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 look at some of the data below. Growth in revenue, tick. Positive impact on productivity, satisfaction and more, tick. And the final thing, companies are willing to pay to develop their leaders.
![]() Source; IBISWorld. | ![]() Source; LinkedIn. | ![]() Source; hallucinations. |
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 a number of 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.
I was never really that great at any one thing, but that’s the point right, to be good enough to get a lot of broad things done. To be a generalist.
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.” This is big for me. In this startup and tech ecosystem we live in there are so many stories of bullshit companies that are out there raising billions to work on what I would call ‘non problems.’ | ![]() Endless Summer 3. |
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 head first off of 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.

JB, Lexy & slime.
The two 15-year old, snotty nosed, pre-pubescents were totally unawares that their 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 back. “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 actually 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.
Facebook was the best education anyone could ask for on how to get things done. They literally installed sensor lights in every office so we could save a couple of seconds thousands of times a day.
Not only had this team worked together before, they had worked at one of the most impressive organisations in the 4 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, make progress. A clear principle taken from the team who 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 archers bow, pulled all the way back to full extension, just waiting to be pointed at the right problem.
I joined Sidebar because as human beings we just spend so much of our lives working. When you make a positive impact on somebody's career, you can just make a huge impact on their life overall.
One person who was critical to the success of Sidebar in the earliest days was Samantha Bergeron. Samantha started originally as a consultant to Sidebar but shortly after came on to be a member of the founding team shortly after. 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. The thing that 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’
The thing that 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 to not just have a few user interview but 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. | ![]() Source; Sidebar. |
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.

Source; Sidebar.
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.
When I go into a Sunshine session I know I’m getting actual sunshine…Being a founder is a very lonely, thankless job, you’re usually being yelled at. Just knowing there’s somebody there checking in on me and cheerleading me and reassuring me that everything is okay is the value of Sunshine.
Another thing they found was structure and programming was 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 quite 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 valuable enough to be part of the product longer term.

“So the GTM plan starts with Google Ads.”
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: One of my groups (I have two) is a great example of this. I have two listed company execs, founders and product people, and a load of leaders in the middle of their career.
And the other thing that was key was that the groups 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 also. Bonkers stuff.
Overall, this was the definition going through a process to find product market. Samantha put it best herself; "Putting the customer at the center... has allowed us to build in a really smart way.”
MVP → Beta launch → Public launch
One great way to validate product market fit is to see if people are willing to pay for what you are selling. "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.
The member that is our sort of North Star customer...is a senior manager who's really director VP level with about 16 to 20 years professional experience. I think probably the most distinctive characteristic of the ideal member is that they are really growth-minded. Members who want to learn and want to get better and want to improve do great at Sidebar.
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.” As 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 would 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.
Number | GTM strategy |
---|---|
1-32 | Project Sunshine (friends). |
33-100 | More friends and family. |
101-200 | “Hand to hand combat by referral.” |
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 was all good VC backed companies did, they ran Meta Ads … unfortunately, unsuccessfully for now.
I worked on paid ads for years and especially like in the performance markets whether it's paid search or paid social those things didn't work great. We tested it and it just didn't seem like it was the right tool for the job.
Asher belief was 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 get in front of better audiences: podcasts and newsletters.
And that's when we started looking at newsletters. Podcasts were a big one also, with the idea that you know people are really reading these they're there to consume content, they're there to sharpen their skill set, and hone their craft. That’s where the intent is much better.
Number | GTM strategy |
---|---|
200+ | Newsletters and podcasts. |
And that really brings us to today. Sidebar’s GTM leans heavily into leveraging great audiences in tech. This newsletter you are ready 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 I do know that they have a waiting list of over 35,000 people today.

Source; My WhatsApp.
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 great pedigree and with a massive desire to tackle this problem head on. Most of which 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, that ws research lead, 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 newsletter usually have a much higher quality audience than other channels. Sidebar was able to leverage this in the early days and are still huge spenders 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 diverse contexts of each role. This lead to an improved matching algorithm that considered the specific daily tasks and challenges or 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.
Why I use Sidebar
This is the first of our new Zero to One series with this newsletter, and I don’t expect to be a paying user of the next set of companies. But I am a Sidebar member, a founding one in fact. I use it because I am ambitious, and I like to surround myself with ambitious people. Simple as that really.
Yes, I value the coaching, mentoring, support, friendship and accountability—especially the accountability. |
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 really showing for themselves. If you, are reading this, then you are probably like me, young(ish), ambitious and keen to have a great career you can look on with pride. | ![]() San Diedo by Andres Garcia. |
Extra reading
You can follow Lexy Franklin and check out Sidebar if you are looking to build and grow your network of peers.

BRAIN FOOD 🧠
Product for Engineers dropped another awesome post recently: How we decide what to build. It’s a beautiful building-in-public look at how PostHog go about product development. There is so much to learn from this newsletter. I love it.

TWEETS OF THE WEEK 🐣
Yvon Chouinard = GOAT of doing business the right way. His book pumps too: Let My People Go Surfing. It’s studied at Harvard Business School.
Yvon Chouinard, Founder of Patagonia, on lame excuses:
— Justin Gordon (@justingordon212)
1:27 PM • Jun 9, 2024
For those who enjoy home office porn.
I designed and built a personal office / art studio in the forest behind my home. Calling it "the nook"
Took 4 months to build.
Let's have a look👇
— Isaac French (@isaacfrench_)
4:03 PM • Jun 7, 2024
And some options data + how we do stock at Athyna.
I don't like stock options. Why do we make people pay to buy a piece of the company they are helping to build?
Why do we have such a glass half empty approach?
At Athyna, we have a 20% RSU pool (not options). I don't want our team to have to pay to buy in at our company. If… x.com/i/web/status/1…— Bill Kerr (@bill_kerrrrr)
4:37 PM • Jun 6, 2024

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 Attio—powerful, flexible and data-driven, the exact CRM your business needs.
See the full set of tools we use inside of Athyna & Open Source CEO here.

HOW I CAN HELP 🥳
Here are the options I have for us to work together. If any of them are interesting to you—hit me up!
🌏 Hiring global talent: Check out my startup Athyna.
🧰 Want to outperform the competition: See our suite of tools & resources.
🏡 Looking for a personal board of directors: Check out Sidebar.
👀 Reach thousands of tech leaders: Advertise with us here.

And that’s it! See you next time. ✌️
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