Funding tactics

Customers rent devices on 24- or 36-month contracts paid monthly with no early exit (e.g. ~EUR 50/month for a laptop). Fleet resells each contract to a bank, which pays the full contract value upfront minus ~10%. Fleet buys the device with that cash and books its margin on day one; the bank carries the credit risk if the client goes bankrupt. At contract end Fleet buys the device back from the bank for a small amount. Because growth needs no working capital, the company was cash-flow positive and bootstrapped for 7 years.

After walking away from a VC term sheet, and with ~10,000 users on the app, ran an equity crowdfunding round on Seedrs (now Republic). Before going live, agreed terms and valuation with a handful of pre-identified angels (2-3 put in six figures each per round); everyone else invests on the same terms, no preferred shares, from as little as ~10. Made a pitch video plus docs and financials; publicly stated what the money would fund. Gave perks: all first-round investors got a Savvy Navvy sailing jacket; another round gave 3-year subscriptions. Set a minimum (enough for the next 12-18 months) and a maximum (to cap dilution) and closed the round when the max was hit. Used the money mainly for B2C marketing. Later taps the 2,500 investors (mostly boaters) for expertise, e.g. logistics or marketing advice. Investors can sell on the platform's secondary market.

Rather than paying cash, take a loan for the purchase price. Illustration: an app making $10K/month profit bought for $350K on a 10-year loan with ~$5K/month payments leaves ~$5K/month profit; price is earned back in ~3 years with 7 more years of loan term. Only buy apps with organic distribution built in, so profit doesn't depend on continued ad spend. Used for Indie App Santa (2024) even though they had the cash.

Measured early UGC returns (ROAS / LTV:CAC ~5-6x, with a constant view-to-download rate per format), then emptied his bank account and took a ~$100K personal loan to pay creators. Scaled at break-even (every dollar in came back out) and reinvested all revenue into growth.

Set the quit line at the point the business covers all personal expenses without burning savings or cutting contractors: ~$20K/month revenue = ~$10K/month profit (New York cost of living). Decided to leave at ~$17-18K/month and gave notice for December; laid off in November with severance. Worked nights and weekends meanwhile, with a 'Ship It Sundays' friend group chat.

Raised while above 20% EBITDA margin rather than out of need. Set the target valuation and terms up front from a share-price model (monthly to 2031) and the buyer profiles that could pay 4-6x the entry price later; higher term sheets did not sway them. Picked the lead (Sumeru) on partnership fit after 3-4 dinners (~12 hours) before the process. Goal: avoid a price that forces an IPO or leaves founders, employees and common holders underwater.

Went through YC with strong revenue and CAC/LTV. Investors sought them out: ~100 meetings scheduled, most canceled after the round closed in ~3 days. Venture money covered negative cash flow from app store payout timing and high voice-AI costs. Partner advice: keep pushing the UGC lever that works.

First deck led with the founder's track record (Rupa 5 to 75M, 4,000% UA growth), ~23K MAU, 762 reviews and a 1M downloads/month dream; it largely failed. Post-YC deck: a big future market, proof of product-market fit and outcomes (users staying sober), positioning within AI, a revenue chart going up (not users), and a letter of intent for a pilot to show a bigger market.

After 3-4 years of failing to fund the idea (even after growing Rupa), put in $100K of his own money and pitched people who had profited from Rupa's exit to invest.

Each founder put in ~$10K upfront; afterwards reinvested App Store and Stripe revenue into creators; ran at ~50% EBITDA margins every month; used startup credit programs for AI costs early, optimizing costs only later.

When the VC cash was running low and the Series A was due, they judged they lacked the metrics (not 200% year-over-year growth). With insider (Founder Collective) support they converted to a breakeven business and have kept growing from profits. Greg advises most one- or two-founder consumer apps not to raise VC; use friends-and-family money (e.g. $20K for test ads) and accelerator SAFEs/notes that don't lock you into the VC path.

Raised a pre-seed from a known investor (Lachy Groom, ex-Stripe solo GP) on the three co-founders and a general direction while prototyping. After the soft launch showed traction, the same lead investor doubled down, making a $10M seed in total.