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Well Spaced - Podcast for Squarespace Designers
New Squarespace podcast is launched!
Ep. 1
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Wayne and Olga introduce themselves and explain why they're launching a podcast together. They met at Squarespace Circle Day in New York (September 2025), connected online afterward, and started chatting so regularly about business that recording it felt like the natural next step. This first episode is a "why we're here" conversation — no deep topic, just origin story and intent.
Key themes in this episode:
- Two very different business models (productized subscription vs. course/template shop) operating in the same Squarespace ecosystem
- The loneliness of online entrepreneurship and the gap in having peers who truly understand niche platform businesses
- Why the Squarespace-focused podcast space is underserved — and why audio + YouTube felt like the right format
Upcoming topics teased:
- Selling to local clients
- Selling templates
- Discovery calls
- Pricing
- SEO
- AI & market predictions
- What clients really want (but don't say)
- Circle designer identity theft scam
- How to pivot your business model
- Squarespace platform updates
More episodes
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5. The secrets of local networking (not awkward at all)
17:47||Ep. 5Olga has built her entire client base online — SEO, templates, Zoom calls with strangers who found her on Google. Wayne gets the majority of his work through local relationships and referrals. Neither of them had really compared notes on this until now.In this episode Olga asks Wayne to just explain it — how does local networking actually work, how much time does it take, and is it worth it for a web designer who isn't naturally a glad-hander? Wayne breaks down the approach he stumbled into almost by accident: joining a local business association, eventually getting on the board, showing up consistently without ever trying to sell anything, and watching trust accumulate until people are three beers into a happy hour telling him they hate their website.The core insight is simple but easy to underestimate: in-person trust builds differently than online trust. When someone meets you face to face, knows your personality, has seen you show up month after month with no agenda, the moment they need a website you're already the obvious person. You don't pitch. You don't hand out cards. You just become the website person in the room.They also talk about where local networking goes wrong — the BNI-style referral groups that feel like speed dating, chambers of commerce so large you could network for years and barely scratch the surface, and the exhaustion of trying to attend every event in town. There's a sweet spot in community size, and Wayne has a pretty specific take on what it is.In this episode: why Olga finds in-person selling awkward and what's behind it — how Wayne's local strategy started out of loneliness, not a plan — the right community size for meaningful relationship building — how long it actually takes before referrals start coming in — why showing up without an agenda works better than any pitch — business cards and why Wayne still has most of his 250 — BNI and referral groups and why they felt gross — chamber of commerce vs. smaller local business associations — meaningful conversations as a trackable sales metric — and why the moment someone says "my nephew built my website" is exactly when you want to already be their friend.
4. The biggest Squarespace scam ever
15:00||Ep. 4This one is personal. Right before recording, Olga caught a scammer actively browsing her website — pulling up old pages buried in the sitemap, not linked anywhere — and within minutes received a fake form submission. One of her clients had already paid money. Wayne has been dealing with this for months.If you're a Squarespace Circle member and you haven't heard about this yet, here's what's happening: scammers are scraping designer portfolios, pulling client contact information from public sites, and sending emails impersonating Circle members — complete with fake Gmail addresses using your real name. The offers have shifted over time, from SEO packages to site audits, but the mechanics are the same. They find your clients, they use your name, and some of those clients pay.Squarespace has responded — they've notified Circle members, reached out to customers, and worked with PayPal and Stripe to shut down payment links — but the scam keeps evolving. An FBI case has reportedly been opened by a Circle member in New Hampshire. The emails are still going out.In this episode Wayne and Olga talk through what they know, what they've done to protect their clients, and what they wish Squarespace would do differently. The practical takeaway: email your clients now, tell them exactly which address you write from, and tell them what you would never offer or ask for. Don't wait for this to land in someone's inbox first.In this episode: how the scam works and where the client data comes from — fake Gmail addresses and how to spot them — how voice and tone is actually catching scammers out — what Squarespace has done and where their hands are tied — the FBI case — PayPal and Stripe shutting down payment links — why the scam keeps working and what that says about client communication gaps — what to send your clients right now — and why this might push designers off the platform entirely if Squarespace doesn't get more aggressive about it.
3. Running a Squarespace template shop
27:04||Ep. 3The truth about selling Squarespace templates (it's not passive income).Selling Squarespace templates looks like the dream from the outside — build it once, sell it forever. Olga has been doing it since 2020 and she's here to set the record straight: it is not passive income. It is a second business running alongside your services business, and if you go in without understanding that, you will probably give up before it works.In this episode Wayne asks Olga everything — the misconceptions, the marketing, the support load, the client surprises, and the moment a template buyer becomes a custom design client. Olga has been selling templates for almost six years, is closing in on Squarespace Circle Platinum status largely on template installs alone, and has made pretty much every mistake so you don't have to.The biggest thing most designers get wrong? Launching a template before they have an audience. Olga's honest benchmark: you probably need at least 2,000 monthly blog visitors before a template shop makes sense. That means 50 to 100 blog posts and a real understanding of SEO before you list a single product. Skip that step and you're building a store nobody can find.They also get into how templates and services feed each other as a funnel, why Olga scrapped 18 individual template courses in favor of one simple guide, how she designs for a niche that almost always surprises her, and why the designers who quit at three templates are the ones who were closest to it working.In this episode: the passive income myth — how long it actually takes to build template sales — blog traffic as a prerequisite — how many templates to launch with — building your first audience vs. building your first product — support, documentation, and where to draw the line — how templates become a pipeline for custom services — designing for a niche and getting surprised by who actually buys — Squarespace vs. Showit vs. Webflow vs. Shopify template markets — why Olga still hasn't given her Showit shop enough love — and what she would do differently if she started over (spoiler: not much).
2. Surviving the busy season
34:36||Ep. 2February 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.