Running multiple ventures shouldn’t mean carrying them alone
When you run more than one company, the decisions multiply and the risk compounds, but the number of people who genuinely understand that load shrinks. Most founder rooms are built for someone with a single venture. This one isn’t.
The Parallel Entrepreneur Network is a private, vetted group of founders who run several ventures at once. It exists so you never have to make the hard calls in isolation, and so the lessons you pay for in one venture pay off across all the others.
What membership gives you
- A room of people who get it. Celebrate the wins and talk through the hard parts with peers who carry the same weight and genuinely want to see you succeed. No posturing, no judgment.
- Collective wisdom on tap. Stuck on a problem? Someone here has already faced it, or knows who can help. You stop guessing and start drawing on a room that has been there.
- Collaboration over competition. These are allies, not rivals. Members trade introductions, playbooks, and honest pushback to build something bigger than the sum of their ventures.
- The parallel advantage, compounded. Systems, hard-won lessons, and relationships transfer from one venture to the next. In the right room, that cross-pollination accelerates.
Who joins the Network
The Network is intentionally small and vetted, made up of founders who run, or are actively building toward, more than one venture at a time. They come at different stages, but they tend to share the same instincts.
It’s likely a fit if:
- You’re running two or more ventures, or building the next one while the first still needs you.
- You’re often the only person in the room carrying this kind of load.
- You’d rather have peers who tell you the truth than an audience that tells you you’re great.
- You see your ventures as one connected system, not a series of unrelated bets.
Membership comes in two tiers, early-stage and later-stage, so the founders around you are matched to where you are. Both are detailed below.
Inside a mastermind
Each month, small groups of vetted founders meet to work through the decisions that actually move the needle, not to swap business cards. You bring a real situation: a hire you’re unsure about, a venture that’s stalling, a deal on the table. Chances are someone in the room has already faced it, and they’ll tell you what they’d do differently.
Between sessions, the community stays on, so a question never has to wait for the next meeting. And once a quarter, you set your goals out loud and let the group hold you to them. The accountability is the point: it’s hard to drift when people who understand the work are checking in.
What’s included
Every membership includes:
- Monthly mastermind sessions tailored to your stage, where you get real counsel on real decisions.
- A private, always-on community of vetted parallel entrepreneurs.
- Quarterly goal-setting and accountability to keep you honest about what actually matters.
- Warm introductions across the network for when you need a person, not just an answer.
- Practical playbooks for managing and scaling several ventures at once.
New here? Start with what a parallel entrepreneur is, or learn more about the Network.
What founders tell us
Across more than 35 conversations with founders on our podcast, the same truth keeps surfacing: nobody builds alone.
They talk about how lonely it is at the top, and they talk about co-founder problems that happen later.
— Caitlin MacGregor, co-founder & CEO of Plum (Ep. 10)
When I joined the CEO roundtable, it was the first time I was in community with people that were like me, a bunch of business weirdos, entrepreneurs doing cool things. And I thought: this is my tribe.
— Robert Hartline, founder who scaled a wireless business to ~$100M (Ep. 15)
If you’re the smartest person in the room, you’re in the wrong room.
— Eve Peeterson, former head of Startup Estonia (Ep. 34)
I loved hearing the other questions that people on the board were asking that I hadn’t thought to ask.
— Carla Bailo, automotive executive & former CEO of the Center for Automotive Research (Ep. 21)
I don’t view any other independent sponsors as my competitors. We may be competing on a deal, but I view them as collaborative people in the same market.
— Douglas Song, founder & CEO of Protos Capital (Ep. 37)
Running multiple businesses is a superpower in itself, because any business I’m running gets exponentially more value from the shared experiences across different verticals.
— Craig Fuller, founder of FreightWaves (Ep. 8)
Find your room sooner
Most of these founders found their room the hard way, years in, often after a lonely stretch they wouldn’t repeat. The Parallel Entrepreneur Network exists so you don’t have to wait that long. Membership is the room, ready the day you join: vetted peers who carry the same load, the monthly masterminds, and the community behind them. Pick the tier that fits where you are today.
