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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91 stories / Side projects. Newest first.

  1. The Long Way HereI build technology companies, work with startups, run and ride bikes, fix old houses, and start more side projects than I need.
  2. All My AI Tools, One DoorI had too many AI tools, too many separate connections, and one web portal trying to put them behind the same door.
  3. I Signed ItNine days after telling people I would probably pass on Pinata, I accepted the Chief Product and Technology Officer role and signed the offer.
  4. It Looked ReadyGetting the Cornwall house ready for short-term rentals meant paint touchups, spring cleanup, a bounced bulk-pickup request, and too many appointments.
  5. 718-400-WOLFA Shopify login, a Printful account, one vanity phone number, and the old coffee-drinking wolf became a real side-project stack.
  6. Poughkeepsie or West?A Hudson Valley rental search and a possible move West were both real plans during the same week back in New York.
  7. My Next Profession?A Red Hook pizzeria near a new running track briefly looked like a runner's bar, pizza place, and entirely reasonable next business.
  8. Open the Next Line SheetApply launched a LACMA collaboration while museum wholesale, production files, and my new Wahoo job all kept moving in the same week.
  9. The Peugeot Got WeirdAn old steel Peugeot frame, a modern one-by drivetrain, and two sets of pedals became my January bike project.
  10. A Miserable WeekTwo home sales ate the week while Apply kept moving and a late Rapchat proposal pulled me back toward music and startup work.
  11. Someday Never ComesA Rapchat architecture review found an old stack, a future rewrite, and a team trying to grow the system it already had.
  12. A Lot of HoursApply was busy, the Poughkeepsie house had a leak and ancient wiring, and I still said yes to helping Rapchat and Cutback Coach. COVID had left a lot of hours in the day.
  13. Pumped To Have You AboardOne early believer decided to back Apply, and the company moved one step closer to turning a very fun deck into a funded business.
  14. It Looked RejectedApply had products, a live Instagram account, and a store nearing launch. The connection between all of them still refused to work.
  15. 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.
  16. The Side CompanyApply Stickers started as a small side business while I was still working full time at Aaptiv.
  17. Runner to Runner :)I wanted old NYRR data for a Prospect Park Track Club side project, so I emailed the runner who built RunGraphs and asked for his scraper.
  18. One Day Between TenantsThe old tenant, the new tenant, one service elevator, a missing form, a missing key, and a very small window to turn over my Williamsburg loft.
  19. List the Loft ImmediatelyAn early lease exit turned my 60 Broadway loft into a fast listing, showing, application, and lease sprint while the building was wrapped in construction plastic.
  20. Very Close, FinallyThe Poughkeepsie rehabilitation was nearly ready for bank sign-off after an unexpected drainage problem held up the work.
  21. The Tub Was on the WayA bathtub, a vanity, one tile measurement, and a scheduled power restoration moved the Poughkeepsie Victorian past another planning phase.
  22. Make It SleepableI could not finish planning the Poughkeepsie house from New York. First it needed water, heat, one bathroom, and somewhere to sleep.
  23. Find the CapitalThe Midwest housing project needed cash, so I started asking whether old startup equity could fund the next thing I wanted to build.
  24. Cancel the ContractMonths of diligence changed the economics at Rustic Meadows. The seller rejected our new position, so we ended the deal and protected our earnest money.
  25. I Needed a Peaceful NightAfter thinking nonstop about an offer from Aaptiv, I declined because I still wanted to build a company from the beginning.
  26. Our Side Was SignedAfter months of park visits, documents, and diligence, we sent the seller a signed purchase agreement before Thanksgiving.
  27. Measure the Concrete PadsBlue Sky's first mobile-home-park site visit meant flying to Missouri, interviewing the manager, checking the records, and measuring concrete pads.
  28. The Park Got RealA rejected Indiana mobile-home-park inquiry led my partners and me to Missouri, a property visit, and a much more serious side project.
  29. Already Under ContractMy partners and I found a mobile-home park in Fort Wayne that matched our plan almost exactly. Somebody else had reached it first.
  30. The Beam Was CutThe inspection on the Poughkeepsie Victorian found a cut basement beam, a sagging floor, and a renovation list that kept getting longer.
  31. Almost Ready to ShowThe side project had moved from an idea I kept describing to something I hoped a trusted friend could try within weeks.
  32. One or Two ParksI was looking at mobile-home parks across the Midwest and wanted to understand why the market felt so inefficient.
  33. Four Buttons, Somehow ImpossibleLoft 2.0 had smart bulbs, a mounted television, and new audio, but the custom light-and-shade remotes took an entire day to find.
  34. Bourbon and Trailer ParksA Thanksgiving trip to inspect mobile-home parks turned into an introduction for bourbon, space landings, and another strange business conversation.
  35. Scala Goes to LAReonomy was finishing a rebuilt data-processing pipeline for Los Angeles while I looked for temporary help to expand the ingestion team.
  36. The Map Became TreesAfter two weeks of deed and easement research, I finally walked the wooded Hudson Valley parcel I was considering for a vacation place.
  37. Right of Way, Not RefusalA possible vacation-home parcel near Woodstock sent me into deeds, easements, flood maps, liens, and one quick real-estate vocabulary correction.
  38. Mail the Key to MaineMy furnished Portland loft needed a renter, a mailed building key, and a phone-based smart key for the front door.
  39. Not a Second JobI started sketching a consultancy network that could create a second income stream without becoming another full-time job.
  40. Sweating, Dirty, Burning ThingsAfter Gisi died, my brother and I started clearing and rebuilding the DeMotte house, and I realized how much I had missed physical work.
  41. Brass Tax and ValueA smarter-home side project had code, possible partners, and plenty of ambition, but not yet a reason to form a company.
  42. Buy the Fischer GroupI announced a thirty-six-month acquisition plan with no supporting details and one smiling emoji.
  43. There's Legs HereA friend had a working prototype for cloud development environments. I wanted to help figure out whether it could become a company.
  44. There's a Startup in ThereOptopus was a little piece of software with enough of an idea inside it to justify lunch.
  45. Someone Should Build ThisA side-project idea started with a simple gap: site-speed tools were expensive, slow, and built for big companies.
  46. Put a Pool in the RiverA floating, water-filtering public pool in New York sounded just unreasonable enough to back.
  47. Seven Months of StartupsIn a fast stretch, I moved from Peek to a hosting company, then joined Shutterstock and kept Ops Dojo going on the side.
  48. Four Days BehindI answered a Volkswagen-van naming thread four days late and suggested Axl.
  49. Ops Dojo, DelawareBy the end of October, Ops Dojo was a Delaware S corporation with equal founders and an unsettled software plan.
  50. Monk Got a LogoMonk Networks was still a rough business plan, but now it had a very orange face.
  51. Outsource the Whole ThingThe early Monk Networks pitch was simple: give a startup an operations department without making it build one.
  52. Done and DoneTwo hours after an advisor asked for a one-page business summary, the first Monk Networks pitch was moving.
  53. New BeginningsI asked an old Beatport executive to help build a managed-infrastructure company on the side.
  54. SuzieQ Had EmailA small fashion business needed Google Apps, two working inboxes, and somebody to explain how to get into them.
  55. The Rows Didn't MatchA database import kept producing the wrong row count during a week that also included illness and a London data-center trip.
  56. The Data Center Needed a CarA consulting job in Somerset required a rental car because I could not find a practical transit route from Manhattan.
  57. Only Young OnceI had a third job offer, a three-person startup that needed to scale, and a very loose theory about burnout.
  58. 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.
  59. Sorry for the Email LookupCraigslist replies had failed me before, so I found the founder's address and made sure my half-time Linux application reached a person.
  60. How Many Tracks?After Beatport I helped think through storage, catalog size, interfaces, and customers for a new high-quality music store idea.
  61. The Marked-Up PlanA clothing-line business plan came home for comments, and I carried the paper copy around until we could go through it together.
  62. Add One SpaceAfter leaving Yodle, I kept helping with its Zenoss monitoring and proposed one space to stop a loose process match.
  63. BGP EstablishedA new autonomous-system number, two network providers, and one multihop setting finally brought the session up.
  64. Two Canceled FlightsNew York interviews went well, but two canceled flights kept me there while Denver consulting work waited.
  65. Rootkit Checks for EverybodyOne compromised consulting server was taken offline for reprovisioning, and I planned rootkit checks across the remaining systems.
  66. My Third JobBeatport, two consulting jobs, and a phone photo sent with one blunt explanation: I wanted a loft.
  67. Delete the Stale LockA noisy MRTG process looked mysterious until the problem came down to one stale lock file.
  68. One Service at a TimeAn after-hours firewall and Linux Virtual Server rebuild needed a simple plan and very short outages.
  69. Twenty Hours, Still GoingA major Beatport deployment had run for twenty hours, and I was still trying to make the meeting for another side job.
  70. I Needed a Night ShiftI was Beatport's IT director and applying for night and weekend data-center work because my family needed more money.
  71. Five VMs. One Desktop.I rebuilt a client's Linux load-balancing setup in virtual machines and tested production-style routing and failover from my desk.
  72. Steve and Barry Needed RAIDTwo client servers with ordinary names needed software RAID, LDAP work, package cleanup, and a lot of careful retracing.
  73. 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.
  74. Fifteen Hours Every Two WeeksMy first consulting invoice came with a request for more hours and a growing list of firewall, colocation, monitoring, and load-balancing work.
  75. The NDA Was SignedOne month after I started looking for extra Linux work, I signed the paperwork for a real consulting client.
  76. A Second Shift From HomeI was Beatport's IT director and answered a Craigslist Linux job with an offer to work remotely at night and on weekends.
  77. A Few HoursMy new reseller hosting account took days to appear while I had web-hosting clients waiting for it.
  78. Still No Welcome LetterI ordered a VPS, confirmed it by phone, and then waited for login details that had not arrived.
  79. Welcome to YouTubeA YouTube welcome message asked me to confirm my email before uploading videos or posting comments.
  80. Renewed. Still Not Launched.An automatic domain renewal kept a name registered for another year without proving a project had launched.
  81. The Domain Renewal PileA fifteen-day registrar notice put another group of old domain names back on the decision list.
  82. The Client Came BackEven after Praxis ended, a former client still needed help finding and preserving old webmail files.
  83. Praxis Kept GoingPraxis was entering its fifth year of systems and network consulting beside my full-time work.
  84. The Test Wouldn't DieBeatport's mail tests continued into December, alongside lingering consulting work and a company that never really closed.
  85. Real Estate, Then ServersOne September day mixed an OptiTrex real-estate side project with a request to discuss another systems job.
  86. I Bought My NameA June 2006 registrar notice confirms that I had registered chrisfischer.info and changed the domain to locked status.
  87. Patch It or ElseMy hosting provider planned to upgrade every managed phpBB forum to version 2.0.20 after new security vulnerabilities were found.
  88. The Website Wasn't DoneA friend asked me to review a dispute over an unfinished website, a forum, contact forms, a logo, and a missed deadline.
  89. Free VPN. Merry Christmas.A former CU colleague sent me OpenVPN, security, and network-tool links while I was working across SimAuthor and Praxis.
  90. Italy Blocked EverythingA network in Italy allowed web traffic but blocked the VPN, SSH, remote desktop, and dial-out access I needed for work.
  91. Who Wants a Gmail Invite?Gmail still required invitations, so I used one of mine to bring a friend and Praxis collaborator over.