Nobody talks about the grind phase | D.Louise founder Jack Zambakides

21 Oct 2026 · 1 min

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In this interview, Matthew Kelly asks Jack Zambakides, founder of D.Louise, to explain the often‑overlooked "grind phase" that early‑stage businesses endure. Jack describes the grind as a period—typically the first one to two years—when the company operates out of a spare room with no team, cash is either nonexistent or fully reinvested, and the founder is constantly juggling cash flow and inventory financing. He illustrates the intensity by recounting D.Louise’s rapid growth from $250K to $1.3M to $4.5M in revenue, explaining how each increase required re‑spinning the same money to purchase inventory (e.g., needing $800K of inventory for a $4M revenue run‑rate with 20% COGS). Jack notes that the cash‑tight, bootstrapped reality persisted for the first five to six years, with the last two years feeling more stable and less of a founder‑only grind. The conversation highlights the emotional and operational challenges of bootstrapping, the cyclical nature of cash reinvestment, and the eventual transition to a more machine‑like operation with a team.

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I think a lot of people see like brands that are doing well like you guys are now, or even made it, like look at Julian selling Huel or whatever, but they assume that there wasn't that. Maybe they just forget that there was the grind phase. I wish I could get there. How would you describe that grind phase at the start? Obviously it's a grind now, but like I think every business has maybe a year or two where it's just in the fucking spare room, no team, maybe there's fuck all cash relatively. Yeah. Or there is cash, but it's all in the business, you can't take it out. How long would you say that period was until it felt like this is like a More of a machine that has a team, runs maybe not autonomously, but less of a founder grind.
I think 100% as bootstrapped, I remember just being like, especially as you're fast growing, like we went from 250 to 1.3 to 4.5 or something like that. You're literally just spinning your money again and again and again. You're making on 1.3, you're making $130K, but then your inventory purchasing for the next year is obviously if you're doing $4 million and you have, I don't know, 20% cost of goods or whatever it is, you need $800K worth of inventory for the year. So it is cash, like cash is tight, cash is hard, and it's probably only really the last— we've been running the business for 5, 6 years— probably in the last 2 years where it feels like we're in a slightly different position. But it's the process. The first year of any business, I would say, is horrendous, like from my experience.