Sep 6, 2022 · 55m · we-live-to-build
30 Virtual Events Later, His Team Still Runs Without Him
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Sean Weisbrot interviews Michael Alexis, CEO of teambuilding.com, about rapidly pivoting and scaling a 90-person remote company during the pandemic, navigating extreme digital nomadism, and transitioning toward personal and professional stability.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 42.7% of the talking time here. How this is scored →
Sean as informed peer 3.3 Guest teaching 2.8 Guest disagreement 0.3 Sean pushing back 0.0
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 54:19 Demarcating appropriate games for team retreats versus personal friends
Michael politely dissents from Sean's practice of playing Cards Against Humanity with company staff, explaining he only plays it with personal friends.
Hardest push from Sean ▶ 49:08 Pressing on executive handling of sudden staff departuresSean drills into what happens when key staff members depart unexpectedly, questioning whether leadership must step directly into the vacuum.
Biggest teaching moment ▶ 35:58 Masterclass in 20L ultralight minimalist livingMichael outlines his ultra-minimalist packing framework with specific gear choices, leading Sean to explicitly concede the minimalist crown.
Sean holds their own ▶ 16:18 Demonstrating superior Mandarin immersion over classroom peersSean explains his deliberate methodology of learning Mandarin entirely on the streets, demonstrating how he surpassed Canadian peers who studied formally for years.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| The Origins and Pandemic Growth of TeamBuilding.com | 3 | 4 | 0 | 0 | Sean asks Michael about his transition from in-person events to launching teambuilding.com during the pandemic lockdown. Michael provides detailed context on acquiring the domain and scaling from zero to 90+ employees. | |
| Embracing and Navigating the Digital Nomad Lifestyle | 2 | 3 | 0 | 0 | Michael recounts why he left his legal career for marketing to pursue a remote nomadic life, ultimately getting stranded in the Canary Islands. The exchange is completely cordial and narrative-driven. | |
| Pandemic Travel Struggles and Remote Podcasting Realities | 4 | 2 | 0 | 0 | Sean shares his own pandemic travel timeline through Vietnam, Miami, and Europe alongside the logistical difficulties of recording podcast audio while nomadic. Michael validates Sean's experience with an anecdote of a failed interview in Beijing. | |
| Early Experiences and Language Learning in China | 4 | 2 | 1 | 0 | Both host and guest bond over arriving in China around the 2008 Olympics. Sean asserts his strategy of street immersion outperformed traditional classroom learning, while Michael explains his motivation for living in China. | |
| Chinese High-Speed Rails and the Infamous Chicken Train | 3 | 1 | 0 | 0 | Sean and Michael compare experiences with Chinese high-speed trains versus slow overnight sleeper trains. Sean recounts his grueling 25-hour non-air-conditioned chicken train journey to Chengdu. | |
| Favorite Global Destinations and Remote Work Hurdles | 2 | 3 | 0 | 0 | Michael reflects on his favorite travel destinations like South Korea and discusses the extreme productivity barrier of relying on slow internet aboard transatlantic cruises. | |
| Cultivating Global Friendships and Serendipitous Encounters | 3 | 2 | 0 | 0 | Sean details his extensive network of expatriate friends across Europe and how he steps directly into local social circles. Michael asks Sean how maintaining dispersed global friendships affects choosing where to settle. | |
| The Philosophy and Discipline of Extreme Minimalism | 3 | 5 | 1 | 0 | Michael explains his extreme minimalism, traveling indefinitely out of a single 20L backpack and detailing an encounter with bewildered customs officials. Sean readily concedes that Michael's minimalist discipline exceeds his own. | |
| Transitioning to Stability and Furnishing Living Spaces | 4 | 2 | 0 | 0 | Sean and Michael discuss the shift toward buying property and investing in quality furnishings like mattresses and desks after years of nomadic living, comparing notes on landlord negotiations. | |
| Executive Leadership, Delegation, and Organizational Scaling | 4 | 4 | 0 | 0 | Sean asks targeted questions about executive delegation, identifying hiring bottlenecks, and managing operational vacuums. Michael breaks down how his company builds redundancy across departments. | |
| Internal Team Building Strategies and Executive Boundaries | 4 | 3 | 1 | 0 | The conversation covers internal team building practices. Sean mentions playing Cards Against Humanity with staff, and Michael gently pushes back, noting he reserves that game for friends rather than employees while acknowledging the need for executive distance. |
Statements from this episode (11)
Alexis: VR interactions feel far more organic than Zoom calls
“Beyond being on a Zoom call on us, Talking, if we're in VR, it's like we're doing something together. We're talking over the headset in a way that feels very organic and in person.”
Alexis: TeamBuilding.com gained first client in 24 hours, was profitable month one
“Within 24 hours. We had our first customer even with the. Kind of harsh hit to the previous businesses. We still finished out that month profitably and then grew rapidly from there.”
Alexis: TeamBuilding.com employs around 90 people
“I believe right now the number is 90. We have full-time staff who are the sales team, marketing customer service, et cetera. And then we have all of our event hosts.”
Alexis: TeamBuilding.com scales to nearly 200 staff during Q4 holiday season
“Quarter four is quite busy for us. As companies are not just doing team building, but they're also doing holiday parties, and so we'll bring on seasonal staff, which pushes us up to more like I think it was one 80 last year, or almost 200 even”
Alexis: Practicing law is poorly suited for a nomadic lifestyle
“It's very difficult to be a nomadic lawyer because your clients want and often need to see you in person, right? Like you have to be there to sign documents, to witness documents, to have Like frankly, very important conversations.”
Weisbrot: Constant travel prevents effectively building a business
“I'm trying to work on myself and my business and like, I can't do that if I'm moving around so much. So I I'm like also kind of going back. It seems like you were, I'm kind of like looking for stability again.”
Alexis: teambuilding.com operates independently without executive day-to-day involvement
“We have a fantastic team of smart, hardworking people who are very capable and competent side from us. And so the business continues to run.”
Weisbrot: Investor in his company met at Shenzhen crypto dinner
“So when I went to Vietnam, I only knew one person and that person is now an investor in my company. But I met him in Shenzhen actually at like a private dinner party for like crypto bros.”
Reintroducing in-person events doubled TeamBuilding.com's operational complexity
“We've also reintroduced in-person events in the last three months and that has allowed us to continue growth. It is also in some ways doubled the complexity of the business. Like we're running two businesses. One is a virtual business. One is in-person events.”
Alexis: Company Leaders Must Make Every Single Task Eligible for Delegation
“As the head of the company, literally everything you do should be up. For delegation. And if there's not a current team member that can take it on, it does usually mean hiring or outsourcing or automation or one of the alternatives.”
Alexis intentionally skips internal social events to give employees breathing room
“I attend some of the team building events and then I intentionally don't attend others. An example of that would be, we have an upcoming company retreat in New York, we're flying everybody in a meeting there. And so there's some of the evening social activitie…”