"Make It Exist": The Founding of Act Two

How we went from zero to company in eight months.

Dan and I will be co-writing a piece on the tactical lessons learned from building Act Two. It’ll be on our company Substack, Citizens of the Internet. My personal reflections are below. I’m back living in Kunming, China for a month, continuing with standup and building Act Two by night. You can watch a clip from a recent set here, or an early clip (w/subtitles) here.

This is the story of how Act Two came to be. From February to October, we went from zero to one as a company, running a five-week cohort for seventy people that ended two weeks ago. After a months of hard work, we now exist.

My biggest takeaway: Learning to befriend uncertainty is the cost of admission for an expansive future. Just be sure you have a titanium stomach for the drops.

“Make it exist.”

I cannot count how many times my co-founder Dan Sleeman and I said this phrase to each other over the past eight months.

It’s February 2025. We want to build a company: something that utilizes our 12,000+ collective hours spent building and delivering high-quality virtual learning programs. But what to build? Maybe a white-glove course-building service for top authors? Or should we try to launch our own thing? Slowly, a vague concept takes shape. We start to feel some excitement.

There’s only one problem: right now, it’s just words. A wisp of an idea in our minds, typed out in a humble Google Doc. We have to figure out exactly what it is. Then we’ll have to make people care.

Make it exist.
____ ____

We have experience in these waters. Dan and I spent years building another cohort-based writing course that helped thousands of people around the world learn how to write and share their ideas online. The program ended far too early, against our desires.

But no matter. Instead of sulking about what we lost, we would move forward and build something new: a fresh vision for helping people use their latent creative potential. We had built it before, and we could build it again.

A new company begins with conversations. Lots and lots of conversations.

At first, they’re between Dan and myself. A partnership was obvious, given our complementary skill sets: I’m Creative Chaos, Dan is Creative Conscientiousness. I lean toward rhapsodic ideas; Dan toward rigorous execution. Ultimately we both deliver on both fronts, and together we’ve made great products that people love.

We also both share visions of a new future for education: Emergent, online-first, experimental, peer-driven, human-based instead of algorithm-based.

We’d been considering starting something together since last summer. At a Starbucks on the Lower East Side of Manhattan, we had sat down and opened up a blank notebook. ‘Company Ideas’, we wrote at the top of the page. We had several attempts last fall. An online academy for blue-collar skills (we plumbed Plumbing YouTube, cold emailed Mike Rowe, and eventually punted). Then we launched a boutique course building productized service and took on our first client. Finally we switched to building “MasterClass, but with Cohorts”, briefly joining a team in Berlin as co-founders. Ultimately nothing stuck.

Cue another Google Doc: ‘New Company Ideas’.

Make it exist.

The Dizziness of White Space

Back to February 2025. Dan and I talk every day, spitballing ideas, brainstorming how we can spin our skill sets and experience into something valuable. It’s hard work.

I cannot emphasize enough the sheer openness of the entrepreneurial abyss when starting over from zero. You can do anything. The only constraint sits between your ears, our ability to imagine: What does the world need? And what can we make? What new entity do we want to weave into reality? In those early conversations, I felt firsthand what they call the “dizziness of freedom” when faced with total creative white space. Vast possibility excites and suffocates all at once.

But some nights we hit remarkable Flow states. One moment stands out: Dan’s in Toronto, I’m living in Kunming, China, working in the empty dining room of a luxe hotel. It’s 2am. The lights cut off two hours ago. I barely notice – we’re onto something. As I pace around the moonlit room, my excitement grows: Help people harness the power of Internet abundance while avoiding its pitfalls. Help people execute on their 1-of-1 creative truth. An Emersonian vision made possible by the Internet. We could call it the “Self Reliance Academy”. We just might be onto something. Now it’s time for feedback.

A Visit from Mike Tyson

We DM friends, former colleagues, and past alumni. We jump on calls with a set bullet points on a doc, a vague concept floating in our minds. We elevator pitch our idea and then listen carefully. What lands? What’s dead on arrival?

30 minute call after call after call, idea after idea after idea. Pages of notes pile up. Finally something starts to take shape. We’ll build an “Academy” to help people harness the power of the Internet. We want to create lasting impact. What if it’s a 12 month program?

After 30 days of calls, we build a deck and rally two focus groups of Write of Passage alums. We’ve been working hard. We start to feel excited, maybe even proud. We present our 12-month academy idea to Focus Group #1 with hope in our eyes. They respond with blank stares and delicately-worded tear-downs.

‘12 months might be a bit…too long.’

‘I’m worried you’re boiling the ocean here…”

‘People seem tired of courses in general. I’m not sure people will want this.’

The verdict is clear: it’s not landing.

As the call ends, Dan and I sit on Zoom. I’m in a godforsaken library in western China at 3am with shaky Internet and a spotty VPN. We stare at each other, bleary-eyed, exhausted, disappointed. This is our Mike Tyson get-punched-in-the-mouth moment. It’s demoralizing to feel your hopeful vision land with such a thud. We face two options: bail, or rebuild the entire deck in 48 hours, before call #2. Deck it is.

We rethink program scope, revamp the value prop, and rework the slides. Tweak, change, tweak, change. The second focus group fails slightly less, but it’s still not clicking. Another gut-punch moment.

As this focus group ends, one person offers to stay on and jam further. Enter Latham Turner, a top alum from the Write of Passage days. Latham is passionate about better education paths for his kids. He’s looking at building a school, or perhaps media about alternative learning options. He talks about his creative process – what’s going well, and where he could use support on the journey. Most importantly, he encourages us: “Just stand up a beta program this summer. Something short. I would join. I’m sure a few dozen other people would, too. You guys can build something good.” In the abyss of not-yet-existing, such encouragement is invaluable. Our bonus chat with Latham is our first turning point, a glimmer of hope.

Make it exist.

“What Do We Call It?”

We ditch the year-long academy and return to a timeframe we’re familiar with: a multi-week, time-bound program to help people kick off their creative endeavors. We’ll offer support to any creative domain, rather than just writing. We’ll help people execute their projects and also tap into the power of the Internet. A new way forward takes shape.

Now we need a name. Through conversations with Dan, Essay Architecture founder Michael Dean, and others, we bat around ideas. Our original Google Doc had been titled ‘Heart Self Academy,’ although it was more meant for positioning - we want to position ourselves against the externally-oriented programs of the chase-the-algo and juice-your-LinkedIn variety. Our first crack at a name is the ‘Self Reliance Academy’: applying Emersonian principles in the Internet Age.

As it turns out, ‘self-reliance’ is also a favorite term of prepper communities (not ideal for SEO). Onward. It’ll be something else. We brainstorm names late into the night. What to call it? What to call it?

We cycle through false positives. “Ember Academy.” “Tenacity.” Nothing sticks.

Finally, one Sunday I trek off to the Bolian Hot Springs an hour west of Kunming. It’s my peace-of-mind getaway spot when I’m in China. As I lounge in the springs, phone-free, I scribble name idea after name idea into a small brown notebook. Suddenly, it hits me. I write down a simple, two-word phrase. I play with it, repeating it over and over. It has a ring…

I text Dan: “I’m starting to get excited about Act Two.”

It’s fairly understandable at a glance, yet vague enough to be intriguing. It’s memorable. It hints at reinvention. And it’s not taken. Ladies and gentlemen, we have a winner.

Armed with our new identity, we continue gathering feedback. Conversation, conversation, conversation. Feedback, feedback, more feedback. We mock up a basic landing page on Squarespace and start to gather live, real-time reactions of the site. On the first call, my buddy Chris calls me out: “ ‘Kickstart Your Next Chapter’ as your headline? Really?! You guys are more creative than that!” He’s right.

The website improves, slow but surely. It’s fairly bland, design-wise. Finally, Dan had a chat with an acquaintance in Toronto who has experience in branding. ‘Your site looks so 2010,’ she says. ‘Make it modern. Make it pop.’ So we do. Well, Dan does. He comes back with a completely new look - bold, in-your-face, bright orange and purple. It takes me a minute, but ultimately I love it.

Finally, on Friday, April 25th, we debut our new Act Two website to the world. It’s a solid reception across LinkedIn, Twitter, and Substack. Hundreds of likes, dozens of supportive comments. It feels good to go public. We have the rough shape of a concept, and we’ve planted our flag in the ground. The world has been notified.

But our work has just begun. We have a site. Now we need customers.

Make it exist.

The Summer of Swings

Remember your first roller coaster? Apollo’s Chariot at Busch Gardens was mine. A purple monstrosity with a vertical 210-foot drop. My middle-school self couldn’t believe it was possible to feel that way. A shocking one-two punch of thrill and fear, the exhilaration and disbelief. The uncertainty as we slowly climbed. The startling rush as we took the plunge.

All summer, Dan and I rode our version of Apollo’s Chariot, over and over again.

It’s trite say “Building a startup feels like a roller coaster.” It lands different when you feel those downs and ups firsthand. The thrill of our first few of sales. The plunge of a negative feedback call. The high of telling others you’re building a company. The oh-so-low stressor of no income, week after week after week.

In May, we hit a big drop. It’s my last night in China. I hop on a call with Dan. He’s just spoken with a Write of Passage alum, one of our former all-star students who had a good sense of what people might want. She’s supportive, but has lots of doubts. How would it work serving all creative domains, not just writing? Would people join an unproven brand with two people who had never been front-and-center leading a cohort before?

If the website launch was a peak, this marks our new all-time low. What are we even doing? Is there any way this thing actually works? Dan and I have a tough conversations about the difficulty of what we’re trying to pull off, and the uncertainty of whether we’ll be able to sell enough seats to make it.

As I board my flight to leave Kunming, these doubts swirl in my head. But we maintain our conviction. We will press on.

My first stop is Riyadh, Saudi Arabia, to visit Najla, another one of our Write of Passage all stars. She’s extremely encouraging about our vision for Act Two, and even introduces me to a friend of hers who might be interested.

From there I press on to Mayakoba, Mexico where I met up with three other friends for a Founder’s Retreat. We’re there for three idyllic days. The host of the trip, Sid, plus Anjan, Rifath and me, talk about it all. On the startup side: demand testing, finding PMF, identity shifts, how to scale culture, overcoming self-limiting thinking. But we also go far beyond business: hours-long talks about philosophy, sensemaking, Pirsig’s “dynamic quality”, AI 2027, media ecology, online communities, bringing the online offline, Jordan Hall and Daniel Schmachtenberg and Game B…it’s a riveting long weekend, for a few reasons:

First, it’s powerful to talk with other founders who sit at the intersection of “Head Self” and “Heart Self” – these guys all build great products, but also are down to break down the nuances of Lila for two hours at dinner. That’s not always the case. After our weekend in Mayakoba we all stay close with a group chat and regular meetups in New York. The trip forges a long-lasting bond that will continue for years to come.

At the same time, it’s also helpful to trade notes with entrepreneurs in the trenches. To learn from those who have stared down the same abyss of uncertainty in the early days. I feel a sense of camaraderie as I shared the highs and lows of building Act Two.

But at times I doubt. Of the four of us, two have squarely found pmf, including Sid’s company, Circle which is closing in on $50m ARR. Meanwhile, I’m stuck on the idea side of the abyss. Act Two is still just a thought, with only a small handful of paying customers, and a long, uncertain road ahead. Do I really belong with these guys? Will we get Act Two across the tightrope to the other side?

Make it exist.

From Travels to Conferences

I arrive in New York. My plan had been to stay for two weeks, then travel back to China for the summer (working at night). But being in the heart of Manhattan lights a fire within me. A rapid series of conversations and coffee chats make me realize that NYC is the right home base to build Act Two. A twenty-person meetup of Write of Passage alums in Central Park only confirms my feelings.

As outlined in my Act Two World Tour recaps (Part 1-2; Part 3), I spend much of June traveling – a quick run back to China to grab the rest of my belongings, plus stops in places like Dubai, Singapore, Hong Kong, and London to host in-person meetups with Write of Passage alumni. I meet up with Paul Millerd, Ali Abadaal, and Anne-Laure Le Cunff, successful creators who were kind enough to become guest speakers and affiliates for Act Two. Their support boosts our credibility, especially for newcomers who haven’t heard of us before.

During these travels, Dan and I are also having ongoing calls with potential students. A few are peak moments. One standout is Linart Seprioto, a WOP alum from the Philippines who “felt the internet” for the first time in our program. He leaves an insightful comment on a LinkedIn post, which turns into one of the most productive feedback calls of the summer. Before long he’s helping Dan and I with marketing efforts in a part-time role. Major highs also happen when I chat with someone who hasn’t taken Write of Passage before but loves the concept of Act Two. We stack up a few verbal commitments. Momentum!

Midway through my travels, I stop back in New York. Dan flies down from Toronto, and we meet up for a day to jam on marketing and product ideas. We’re joined by Louie Bacaj, yet another Write of Passage all-star alum and mentor, who lives in the area. He has given us some of the best feedback on the business model up to this point. We chat for the day, and agree to have Louie join as a part-time partner to build the Vibe Coding track of Act Two, while also helping us think about the big-picture business strategy. His experience co-building the Small Bets community proves to invaluable – they cracked always-on community. Pairing his knowledge with Dan and my experience building five-week cohort sprints will be a potent combination.

____ ____

At a private conference in Canada in late July (IP3), uncertainty looms.

We’re six weeks out with ten sales locked in. We need around 50 to be viable. Dan and I have started to have some tough conversations about the way forward if we don’t start making more sales. In certain moments it gets bleak.

The conference is held in breathtaking Victoria, Canada, hosted by entrepreneur and noted Twittersphere figure Andrew Wilkinson. I feel lucky to be there; it seems everyone has a mega-win hiding in their back pocket. “Oh I work on video games.” (Co-founder of Farmville). “I’ve been traveling since I sold my beverage brand.” (Healthade Kombucha).

Meanwhile, when it’s time to share what I do, I talk about Act Two. In that moment, when I feel the least certainty that we’re actually going to make it, I have to show supreme confidence while pitching it to others. Some attendees give honest and critical feedback. They (fairly) question whether the “build-any-project-you-want” model will work, or if we can spark up enough sales without a large audience.

But the conference leads to newfound momentum on a new side of the business – a B2B course-building offering. Conversations that week, particularly with creators with audiences, helps us realize we can spin up a whole different wing of the business simultaneously to drive revenue as we find our footing with Act Two.

Soon, A2 Studios is born. In the weeks after the conference we find ourselves with five different B2B opportunities in progress. The new direction gives us even more confidence that we can create the cash flow necessary to survive into the future. But we still don’t know if Act Two will ever leave the launchpad.

Make it exist.

Staring Down Our Doubts

As July turns to August, we’re starting to seriously worry about Act Two cohort sales. Discovery calls often go well, but the program doesn’t start until September 3rd. We don’t have early-bird pricing. There’s little sense of urgency for people to buy a month in advance. We get lots of “This sounds great, I’ll think on it and let you know!”

We had a goal of 25 enrollees by the end of July. The date comes and goes, not even close. Enrollments are closer to 10 than 25. The financial pressure starts to wear on us. We have a number of tough conversation wondering if this is the right direction, if we’re taking too big of a swing, if we should’ve beta-tested a smaller version first.

In early-to-mid August, sitting at 15 purchases, we face two critical moments of doubt:

• Monday, August 4th: I’m in Toronto for an in-person meeting with Dan. We spend the morning talking big-picture. The vision is resonating with people in conversation, but sales are slow. Should we even run the cohort? Can we even run it? What will it take to get a minimum viable version off the ground? We have a serious conversation of what it would look like to downscope into a self-paced offering, or call it off entirely.

• Thursday, August 7th: My first day officially living in New York. After a couple of promising in-person B2B meetings, Circle founder Sid Yadav and I hop in an Uber to cut across town to the Crane Club, a fancy dinner spot on the west side of Manhattan. I talk to Sid about the newfound momentum on the B2B side, and the lack of sales momentum for the cohort. “Dan and I have been talking, we might shift to a slower-burn always on consumer offering, and focus more of our attention on the B2B side.” Even as I say the words, I know it sounds soft.

To his credit, Sid immediately pushes back: “Dude, do not do that. You have to run the cohort! This is your mission, this is what you’re passionate about. You’ve already come this far. Do not give up!” We talk about minimum viable numbers. We’d been hoping for 50 sales, but given our slow progress, I say that a cohort between 30-40 people could theoretically be viable. But it’ll be thin. “Aim for that,” he says. “You can hit those numbers. You’ve gotta run the cohort.”

With this encouragement we press on. We’ve been tweaking the website all summer, but right around this time, we land on a new, narrower framing for our H1 Header: “Finally Follow Through on That Creative Project.” By emphasizing less the big-picture transformation of a Second Act, and focusing more on the value of creative follow-through, we think we’ve found on a clear message that will resonate with people.

Another key moment comes from a “friend of the program”. Paul Millerd, author of The Pathless Path, is fully aligned with our vision. While hanging out with him in Chiang Mai, Thailand over the summer, he makes me an offer: “I’ll help you launch Act Two however I can. Mentor sessions, an announcement in my newsletter, whatever you need.” This kind of support is so meaningful at our early stage. In July, he includes a personally-written note about Act Two at the top of his newsletter, and why he believes in us. His subscribers complete an interest form. Now, a few weeks later, the enrollments finally start to come in. In the second week of August, seven people from Paul’s audience enroll in Act Two. That pushes us north of 20 students for the first time. Despite these humble numbers, it’s a turning point. Now that we’re past 20, we can see 40 on the horizon, which is where we need to land. In hindsight, I’m not sure Act Two would’ve made it to the finish line without Paul’s support, and I’ll always be grateful to him for that.

Make it exist.

From Zero to One

As August wears on, we start building out the product: the live session skeleton, the community architecture, the weekly cadence. Sales calls continue in parallel. Sporadic enrollments start to drip through, including some all-important purchases outside of our past alumni network. Harrison Moore, yet another all star Write of Passage alum, jumps in to help us spin up a coaching program during the cohort, as well as brainstorm product components. It’s a welcome boost. Other alums offer to pitch in and help as “Ambassadors” to welcome new students in and offer their support. This group includes Karena de Souza, Sandra Yvonne, and Justin Lind. All of this is further momentum.

We also start to run marketing workshops. Louie takes the lead in running three vibe coding workshops in August. It’s a new challenge: teaching a technical skill (Claude Code) in a Zoom environment, but we start to get the hang of it session by session. Two other alumni, Chris Wong and Chao Lam, jump in to help Louie on the vibe coding side.

Meanwhile, Dan and I build an Act Two “Test Drive” marketing workshop session. We get north of 50 registrants, not a bad number. It’s my first time being “the guy”, the primary instructor for the session (as I played the co-pilot role in past programs). It feels meaningful to teach the mindsets that Dan and I developed ourselves: Anchor to the Internal, Head Self vs. Heart Self, and Established vs. Emergent. The workshop goes well, and a few more purchases come in. With a few days before the sales cart closing, we’re north of 30.

From our experience building past cohorts, we know the typical purchase pattern is that up to 50% of sales come in the final 48 hours of the sales window. But there’s no way to guarantee that pattern will hold, especially with a new program. We wait with anticipation as the 48 hour window approaches…

Make it exist.

And sure enough, the sales start to roll in. People we know (alumni, workshop attendees, sales call attendees), but also people we don’t know at all. The purchases keep pinging our Slack tracker. On the night that the sales cart is officially closing, I sit in my NYC sublet, refreshing as midnight approaches – 46…47…48…then suddenly, in a four-minute stretch, four people buy at once. 52 seats! We’ve crossed our magic line of 50. It’s a huge psychological win. We’re officially viable. I throw my arms up in private victory, filled with gratitude.

The cart officially closes Friday night, but per usual, we keep a private enrollment link live for late-joiners. And they keep coming in droves. Some emails, some last-minute calls…people continue to buy. The cohort kicks off on Wednesday – on Tuesday afternoon, we hit 70 enrollments. 70!

Dan and I press hard to build the first 90 minute live session. We pull together slides, frame out the opening mindsets, create the opening “Letter to Yourself” assignment, and run through last-minute dress rehearsals.

Then, at 7:00pm ET on Wednesday, September 3rd, Act Two officially begins. Seeing all of our students on the Zoom grid fills me with a surreal feeling – “It’s actually happening!” I lead the group through opening mindsets and exercises: Creative White Space, Anchoring to the Internal, the Letter to Self. The session runs like a Swiss watch. People raise their hands and share. Energy is high. The ring light feels hot on my forehead as I lead the final group discussion.

To close our first-ever live session, I share the brief remarks of Emerson, my trusted mentor through time and space. He calls for our students not to worry where their creative path may lead, but to live and work, live and work. We all have five weeks together to do exactly that – to launch creative projects, to meet great people, to make the thing only you can make.

The session ends. I shut my laptop. And for just a moment, before hopping on the debrief call, I take a moment for myself. I stare into the bright ring light, revel in the energy of the session we just ran, and even more so, the feat Dan and I just pulled off. From the wisp of an idea to a seventy-person cohort. All the doubts. All the uncertainties. All the moments of nearly bailing that we kept pushing through.

In that moment, I feel it all at once. It’s one of the happier moments of my life. I swell with joy.

We did it.

Act Two exists.

A big thank-you to our Act Two Founding Members. More to be shared soon about your projects and breakthroughs in Cohort 1. Thank you for taking a bet on us.

I also owe a debt of gratitude to so many for feedback and support this entire time. You know who you are.

For now, I’d like to say thank you to Michael Dean and David Sherry for endless hours of conversation that helped bring Act Two to life.