Chris Fischer

Wolf of
Williamsburg

We’ve all heard of The Wolf of Wall Street. Williamsburg is not Wall Street.

I spent most of my tech career living and building in this neighborhood. I watched it change, and changed right along with it, while staying curious enough to chase every crazy idea that came along. Success was always more about the journey and the stories than the big payday.

This page is the timeline of that. Every company, side project, business, property play, hustle, and ridiculous commercial idea I’ve tried. The ones that worked, the ones that failed, and the ones that never made it past a conversation.

Right now I’m the co-founder and CPTO of Goodword, an AI relationship management platform. I’m also continuing Wolf Works, my growth and AI advisory practice, and launching Wolf Works Labs, an incubator and accelerator for early founders who need someone to build their MVP and help them raise financing.

Wolf of Williamsburg in a black beanie, shirt and tie, black trousers and simple shoes, holding a steaming coffee

The endeavors.

The jobs, the companies, the side projects, and the things I keep coming back to. A lot of these were happening at the same time.

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59 stories / Marketing & ecommerce. Newest first.

  1. Who Am I Missing?The inbox knew people the address book had forgotten, so we tested whether two-way conversations could find the gaps.
  2. Hunting Product HuntA Product Hunt launch added screenshots, copy, timing, and one more public door into Goodword.
  3. Three Addresses, One InboxSupport, feedback, and general Goodword email all needed to land somewhere the team would actually see it.
  4. One List, Too Many ToolsAn opted-in email list needed a reliable trip from Google Sheets through cleanup and into Goodword's working CRM.
  5. You're InvitedThe Goodword beta was live. The invitation still had to make people want to connect their real accounts and try it.
  6. Ship First. Email Later.The Goodword update had to be live and checked before the announcement sent people looking for it.
  7. Please Deliver the EmailGoodword's email needed another pass through authentication and delivery before I trusted it to reach an inbox.
  8. @goodword.comGoodword work was spread across old accounts, so we started moving the company and its shared tools onto one email domain.
  9. First EmailA May test message marked the beginning of a new company email setup before the Goodword beta announcement.
  10. Hello, Support?A March email checked whether the first support ticket and reply path worked from end to end.
  11. Real Email AddressesA small startup team started moving from personal accounts to company email.
  12. 718-400-WOLFA Shopify login, a Printful account, one vanity phone number, and the old coffee-drinking wolf became a real side-project stack.
  13. Achievement UnlockedWeek two at Wahoo mixed subscription and running-product work with a stuck Apply marketplace integration and plans to crew the Leadville 100.
  14. Welcome Home. Get to Work.I picked up keys to an Atlanta apartment, started leading Wahoo's subscription business, chased my moving truck, and kept Apply moving too.
  15. Sorry for the Long DelayApply had licensed art, partner payouts, and more than a year of reporting I needed to get squared away.
  16. 1,153 Beta FormsApply Stickers opened a six-day beta signup, collected more than a thousand mailing addresses, and turned my inbox into a Typeform notification machine.
  17. All Hands on StickersApply launched into an ecommerce order spike, a broken payment method, finished financing, and a bubble-mailer shipment waiting on customs.
  18. We Are OfficialApply launched its 2020 voting-sticker campaign, then the founders stayed close to the support inbox and the first shipping questions.
  19. It Looked RejectedApply had products, a live Instagram account, and a store nearing launch. The connection between all of them still refused to work.
  20. Averages Won't WorkA clean churn chart hid the real questions about who was exercising, who was renewing, and whether the product had become a habit.
  21. Order #1001Apply's first Shopify order was mine: three stickers, two notification emails, and a launch still a few weeks away.
  22. Pack Up And Price UpApply Stickers had a bright yellow financial model, a two-to-five-dollar fulfillment problem, and a lot of COVID assumptions to test.
  23. The Side CompanyApply Stickers started as a small side business while I was still working full time at Aaptiv.
  24. Sixty People, Two Hundred ThousandAaptiv had reached about 60 people and 200,000 paying members. I was recruiting, reviewing Peloton, and logging searches that returned nothing.
  25. The Offer LandedA December engineering offer moved through questions, missed calls, and benefit details before the candidate chose to join Reonomy.
  26. Nine Months, Crazy ShitA year-old introduction resurfaced after nine months at Reonomy, and the company already felt both brand new and a decade old.
  27. The Director Search Woke UpAfter pausing the role in September, I spent early December turning engineering-leadership referrals into calls, breakfasts, and real conversations.
  28. Delete My 1:1sReonomy's product and engineering teams had grown, so I replaced a crowded recurring calendar with open office hours and regular goal reviews.
  29. $2 Million Before MidnightThe last day of 2013 ended with major infrastructure orders, spare transceivers, and the practical consequences of a year-end deadline.
  30. We Needed More HumansA June recruiting email described Shutterstock's WebOps team as it looked for operations engineers for the company's next phase of growth.
  31. Bring Him InA technical recruiting conversation moved from an introduction to a phone call to one short decision.
  32. Quiet Rack, PleaseThe new office equipment had two requirements: keep it enclosed and do not make the room sound like a data center.
  33. Boston Takes the TrafficThe web servers had moved. Next came the part customers could actually hit: production traffic.
  34. Make It FasterA new Akamai product might speed up more than static images. First, it had to work on the real site.
  35. Moderately CrazyShutterstock had grown. The office network had grown with it, just without much of a plan.
  36. The Graph DroppedA speed release aimed at distant users landed, and the first measurements moved in the right direction.
  37. Two More CabinetsI asked our provider for one or two short-term data-center cabinets, preferably month to month.
  38. Contributors Couldn't UploadAn upload-server issue blocked part of the contributor base while the team restored storage and explored a reroute.
  39. OutstandingMy performance review came back marked outstanding, with a raise behind it.
  40. Get AggressiveI wanted to move the MogileFS conversation from research toward the real Shutterstock and Bigstock libraries.
  41. Typos Were InfrastructureThe DNS migration started with a long inventory of domains, brand variations, and names collected over time.
  42. Everything Was My JobMy responsibility list kept growing until the breadth of the role became the problem.
  43. I Officially AcceptedThe second conversation with Shutterstock ended with a Director of Systems Operations job.
  44. Let's Make It HappenThe music-store side project had a team, a rough market, and enough of my schedule cleared to begin after New Year's.
  45. Sent from My PeekA five-word Peek-device email asked whether the previous test had arrived and how work was going.
  46. Eight Hundred Ninety-Two PercentI applied to Yodle by comparing its rapid growth with the systems I had already scaled at Beatport.
  47. PTR Records. ASAP.A reverse-DNS failure stopped a consulting client's production mail and turned a long domain list into an urgent provider ticket.
  48. One License. Twenty-Seven Countries.Beatport and Buma/Stemra announced a pan-European music license intended to cover the full European Union.
  49. Deadmau5 Won Most of ItThe first Beatport Music Awards turned a year of store sales and six weeks of public voting into 19 winners.
  50. The Signature Was LongerMy Beatport email signature had grown into five products, two phone numbers, a trademark, and almost no actual message.
  51. Customer CornerViaWest featured Beatport beside Mozy in its customer newsletter while I managed Beatport's hosted infrastructure there.
  52. Beatport Added BeatportalBy late August, Beatportal was live with news, reviews, podcasts, events, streams, and community submissions around Beatport's music store.
  53. The Client Came BackEven after Praxis ended, a former client still needed help finding and preserving old webmail files.
  54. I Was Literally in the OfficeThe funniest line in a month of mail tests was an out-of-office reply explaining that I was actually sitting at work.
  55. I Wasn't Actually AwayAn outside Gmail message triggered a test response from Beatport's vacation responder.
  56. Mail Logs ForeverBeatport's early email setup required a week of tests across queues, lists, outside addresses, and vacation replies.
  57. New Account. Same Tests.A new work account went through the familiar ritual of sending mail back and forth until both directions worked.
  58. Still Testing EmailRepeated test messages between my personal Gmail and SimAuthor account show a month of checking the mail path in both directions.
  59. Test. Test. SimAuthor.A short run of test messages in November 2005 shows me checking delivery between Gmail and SimAuthor accounts.