February hit different this year. Both of us went into the month expecting the usual seasonal uptick — and instead got leads every single day, sometimes two before lunch, working through weekends just to keep up with delivery. It was exciting and completely overwhelming at the same time.
So that's where we start: what does it actually feel like when business is going well but your systems aren't ready for it? The bottlenecks, the guilt, the middle-of-the-night anxiety about keeping clients happy, the moment you realize you are the business's biggest bottleneck. Wayne is actively hiring. Olga is rethinking everything she built.
That leads into a bigger conversation neither of us expected to have — what kind of business are you building, and for what end? A freelance practice you wind down quietly at 65, or something with a real exit multiple? Wayne has been thinking about this for a while. Olga is hearing it for the first time and it lands.
We also get into Squarespace memberships and why building a sortable member directory inside the platform is harder than it should be, how Wayne ended up recreating a third-party community tool in about 30 minutes using Zapier tables, and a heads-up for anyone using social proof widgets on sites with California or EU traffic — the GDPR exposure is something most designers aren't thinking about.
In this episode: the February lead surge and web design seasonality — being booked out vs. being ready for it — hiring and removing yourself as a bottleneck — SOPs, automation, and fixing systems during slow weeks — exit strategy for freelancers vs. agencies vs. productized businesses — valuation multiples and what your business is actually worth — Built to Sell by John Warrillow — the emotional rollercoaster of running a business day to day — ADA compliance lawsuits and ambulance-chaser tactics — Squarespace membership limitations for community directories — Member Space, Community Box, and why Wayne walked away from both — rebuilding a member directory with Zapier forms and tables — social proof widgets and GDPR liability — Howl's Moving Castle as a surprisingly accurate business metaphor.
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