NOW OPEN
Welcome stackers and cowboys to our biweekly edition of this Sellers & Business Club series!
Here, you'll find everything you need to move faster, sell smarter, and stay ahead of trends—with useful insights for every step of the way, community-powered learning posts, insights, and support from other sellers.
Find yourself in the right place, if you're serious about growing your sales, or starting a new gig, stay with us!
What are you trying to improve or accomplish?
Questions? Critiques? Wild ideas?
→ Reply below! We’re all ears.
đ“…¦: https://njump.to/50735c322adf0136dc7f4c64fa4e7f46b0b53574506a44ad6e963c5cff029dcb
Been a while since I rapped at ya. When I last checked in I was launching a new business in the electrical sector and I was trying to ramp up fast with a couple big clients. I talked a big game about contracts I was about to sign and then got busy with work and never gave the update on phase 2. So here it is.
Phase 1 goal was to get launched with our first big customer and lock in at least $1mm in committed sales. We did that and then some. Customer loves us. We're over delivering and undercutting competitors. They keep increasing our remit. They started expanding into another state and gave us new contracts for that state.
Phase 2 was rushing a product to market to take advantage of an opportunity to lock in some ARR. That has not gone as well. I thought we would nail that fast and sell it to our existing customer then use that to find a bigger market. I predicted first sale in 30 days. It didn't happen for many months. And it was much smaller than predicted. We're still under water on that product. But! The sale did happen and we're growing it slowly. We have a strategy for making it essential by giving it to customers for free for the first year and then convincing them to keep it instead of switching to another vendor. So far that is promising but we've not realized sales yet. Too soon to tell.
Phase 3 was suposed to be "find more customers" but turned out to be "expand with our one big customer and service some small customers to get our name out". That's going well and today I have a pitch that might be big customer number 2. This is ambitious and we might have hard choices to make:
And finally, we are both having too much fun at our day jobs to quit them but running two companies and serving on a few boards is slowly killing me. At what point do we face the reality that we have to actually focus on just this for a while?
Current revenue is meh. It's a part-time job that throws off six figures, so meh is not so bad. We're making decent money and there's a lot of promise but growth is a little stalled. Maybe I should stop trying to grow it -- I could just lock in a little ARR with customer 1 and go do other things. I hear bird-watching is fun.
Or I can take the big swing, bet the company, and see where that takes me.
Howdy @fauxfoe, good to hear from you again! 👊
First: Phase 1 exceeded expectations, and the client is already expanding their scope into new states. That's not just "done"; that's a compounding flywheel. You've locked in $1M+ in commitments, and they're actively growing that figure. The foundation is working as intended. As for Phase 2, while the product is currently underwater, the "free-first-year" strategy is a smart wedge. You aren't forcing a new product into a cold market; you're leveraging an existing, trusted relationship. The fact that the initial sale was smaller than expected is a proof point, not a failure. Stick to the one-year commitment—don't let being "underwater" lead you to abandon the project before the retention phase can take hold.
Now, the real question you're sitting with:
Big swing vs. medium swing.
Here's how I'd frame it: the big move isn't about whether you can handle the project; it's about whether you can survive the downside if it falls through. If the contract is smaller than expected after you've already sunk costs into it, do you have six months of runway to find your next client? If yes, take the shot. If not, go for the medium-sized project and let the bigger opportunity come to you—because a client who sees you nail a medium engagement is far more likely to trust you with the big one later. You're already over-delivering and beating the competition; that reputation is your moat.
On the day jobs and burnout.
Take that as a signal. The day jobs are funding the optionality. The question isn't "when do I quit?" It's "what's the trigger that makes the day jobs no longer need?" For most people it's: 12–18 months of revenue that covers personal burn + operating costs, consistently. If customer #2 closes at the big number, you're probably 6 months from that line. If it's the medium number, maybe 12. Either way, you quit whenever your are comfortable with the math.
And the bird-watching comment? Made me laugh lol. But I hear you, the temptation to "just lock in customer 1 and coast" is real when you're running on fumes. The antidote is to stop doing everything at once. My suggestion would be to drop a board seat. Defer a side project. Give yourself one 48-hour block a week where you're not "on." You don't need to choose choose between all your current obligations and the ones that actually move the needle. Not between between ambition and sanity!
Keep us posted. Look forward to see next update being "We signed customer #2." I'll be here. đź’Ş
Big swing didn't materialize. But instead they told us they want to be customer #2. I learned something in that meeting: my business partner is a natural at sales. He's never had a real sales call before and I gave him a ton of coaching, but I'm not sure he needed the help. He had the feel for it. We made the sale early in the call and he just spent the rest of it exploring scope. I spoke substantively just twice and never felt like I needed to take control. It was a warm call, an old contact of his, but still. He nailed it.