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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99 stories / Houses. Newest first.

  1. Both Bikes, NaturallyA February maintenance note covered a new bike build, an older road bike, shifting, the drivetrain, and a saddle swap.
  2. The Grill Learned BreakfastA new propane burner and three attachments turned one patio grill into a searing box, pizza oven, and flat-top breakfast station.
  3. The Couch Finally ArrivedRockaway finally had a real couch, a pullout bed, and one less reason to call the condo unfinished.
  4. Does Thanksgiving Need a Couch?The Rockaway condo was still half moved-in, but Thanksgiving was coming anyway.
  5. Thanks for the Reserve PoursA west-coast vacation produced a winery photo, two PEJU receipts, and one thank-you note for the extra tasting.
  6. Simplifying, ApparentlyA Rockaway closing, a cash offer in Cornwall, two Highland land plots, and one small balcony went into the same July spreadsheet.
  7. I Missed the ContractThe Rockaway closing packet had contracts, riders, disclosures, wire instructions, and one completely unsigned contract.
  8. The Fire Pit StaysA verbal Rockaway offer came with nine patio items, one mortgage contingency, and a spreadsheet for what stayed.
  9. How Long Until Zillow?A two-night Rockaway Beach weekend turned into open houses, neighborhood research, and a 70-page park plan.
  10. 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.
  11. The Houses Dad BuiltA 68-page scan of old construction photos arrived just before Norm Fischer died, then came back into view at his celebration of life.
  12. 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.
  13. 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.
  14. Not Much of a BedroomA new KICKR turned one corner of the New York apartment into the place for early rides before work.
  15. 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.
  16. The House Came With a ListThe first weekend at the Cornwall house included a couch, a grilled dinner, a rainstorm, and a project list before most boxes were open.
  17. Burying the Lead a BitI applied to Chicago Booth without an undergraduate degree while a Wahoo offer, a house purchase, and Apply all kept moving.
  18. Potentially Bringing a BikeA Wahoo visit in Atlanta collided with a house purchase in Cornwall, Apply work, and one very important packing question.
  19. Not Out, But Mostly EmptyA 65-mile ride to Cold Spring led into a storage pod, movers, and one weekend spent consolidating the house without quite finishing the move.
  20. The House Still WorkedCalifornia work kept pulling harder, forcing a choice between ending a Cold Spring rental I loved or finding a careful way to keep it.
  21. Just Coming Back From VacationA California weekend with Amanda ended in a week of Apply production, Wahoo interviews, new startup conversations, and a house that fell through.
  22. The Fun HouseA rushed Hudson Valley house offer pulled Amanda, Eva, lender paperwork, and a possible new version of home into the same three days.
  23. Really Anything Would HelpI rented a Newport Beach apartment I had not seen while TRX product briefs and fourteen-hour meeting days filled the week before move-in.
  24. Are We Done?!Five years after buying a damaged Poughkeepsie Victorian, the permits cleared, the final papers were signed, and the house finally closed.
  25. Newport Pool PartyA Newport Beach apartment turned the new TRX job into a real split-coast routine while Apply and New York kept moving.
  26. Far Beyond ExpectationsAn egress window, rebuilt porch footings, a full trash-out, and an impressed inspector pushed the Poughkeepsie house toward one more showing.
  27. The Offer and the DumpsterThe TRX offer arrived while I was packing the Poughkeepsie house, comparing movers and storage units, and trying to put Apply's value proposition into plain English.
  28. Amazing Team, A Lot of WorkA visit with the TRX team in Newport Beach left me excited about the brand, clear about the hard parts, and ready to talk through the offer with Amanda.
  29. Maine Wanted Wet InkThe sale of my first Portland apartment needed a physical deed, a second notary run, and an Apply call moved at the last minute.
  30. 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.
  31. They Hadn't Seen ItThe Poughkeepsie house got an offer three days after listing, before the buyers had walked through it and before the permit mess was finished.
  32. The House Was Mostly EmptyAfter years rebuilding a wrecked Poughkeepsie Victorian, I cleared it out, argued for the simplest permit path, and booked the listing photos.
  33. The Product Test Was a WorkoutApply was launching, I was moving apartments, and my TRX homework involved live classes, sore muscles, and a lot of product notes.
  34. 318 Active DaysStrava counted 4,573 miles in a year with almost no racing, while I arranged two moves and started new conversations with a Brooklyn run team, TRX, and Cutback Coach.
  35. 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.
  36. First, Fix the DuctsTwo weeks before Apply's launch, I turned an old house's HVAC work into three phases so one expensive problem did not stop everything else.
  37. Mail Back the Bike KeyCOVID put me in the old Poughkeepsie house for real. A few days later Aaptiv asked for the bike-locker key and a decision about whatever was still on my desk.
  38. A Ridiculous MonthPart of the ceiling came down, the repairs became my job, and our temporary move to Poughkeepsie stopped feeling very temporary.
  39. The Gutters Fell InThe Poughkeepsie Victorian started leaking during lockdown while I finished references, left Aaptiv, and weighed a CPO offer from Equinox Media.
  40. God Awful, Works GreatA torn plantar plate put me in a boot. The ugly shoe balancer fixed my hip while I coached 187 runners from the sideline.
  41. Great. Over One Hundred Bats.An inspection found more than 100 bats in the Poughkeepsie attic. I called the exclusion plan reasonable and told the contractor to start.
  42. Not Allowed to QuitThe crew plan for my first Vermont 100 was simple: bring food, track the math, and do not let me make bad decisions.
  43. Still Alive, Mostly RunningWork, the loft, and basic life admin were a mess. Early runs, commute miles, the Armory, and a winter trail day were still happening.
  44. Second Was the PlanI traded the Fifth Avenue Mile for a small Peekskill 5K near the house, brought a faster friend, and aimed for second overall.
  45. 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.
  46. 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.
  47. Very Close, FinallyThe Poughkeepsie rehabilitation was nearly ready for bank sign-off after an unexpected drainage problem held up the work.
  48. The Battery Door BrokeA broken battery door put my Stages power meter out of service until a replacement cover and O-rings arrived.
  49. Take the Cassette ApartI signed up to learn bicycle maintenance, pulled apart a rear wheel, and ended the day debugging a power-meter update.
  50. My Cell Worked InternationallyAmanda and I moved through Berlin, Prague, and Warsaw while Aaptiv hiring and a half-renovated Poughkeepsie house kept reaching me.
  51. 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.
  52. Make It SleepableI could not finish planning the Poughkeepsie house from New York. First it needed water, heat, one bathroom, and somewhere to sleep.
  53. Open the Door RemotelyA possible leak below my old Portland loft turned into a fast remote response while I was living in New York.
  54. 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.
  55. After Work Kept GoingMy move to Aaptiv happened faster than I planned, while spinning, a stress fracture, apartment repairs, and friends' startup questions filled the edges.
  56. 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.
  57. Our Side Was SignedAfter months of park visits, documents, and diligence, we sent the seller a signed purchase agreement before Thanksgiving.
  58. The Tank Was the ProblemA tight powder room turned one toilet into a week of measurements, water-pressure questions, and old commercial plumbing.
  59. 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.
  60. I Put in NoticeI put in notice at Reonomy, watched the organization change around me, then chose to stay long enough to protect the mobile-home-park deal before flying to Paris.
  61. 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.
  62. What Else Do You Need?After weeks of closing paperwork, the Poughkeepsie conversation finally changed to permits, power, and what the contractor needed to begin.
  63. The Last Thing for UnderwritingA missing title company, another contract extension, and one final bank request kept the Poughkeepsie house almost ready to close.
  64. 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.
  65. 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.
  66. One or Two ParksI was looking at mobile-home parks across the Midwest and wanted to understand why the market felt so inefficient.
  67. 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.
  68. Toilets Would Be a Huge WinChristmas break at my childhood home meant exposed plumbing, gas-line work, bathroom floors, and an ambitious hope to install the fixtures.
  69. Bourbon and Trailer ParksA Thanksgiving trip to inspect mobile-home parks turned into an introduction for bourbon, space landings, and another strange business conversation.
  70. Address In, Property ID OutA custom address translator was nearly ready to connect a customer's loan system with Reonomy's property data.
  71. 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.
  72. Ownership, Meet SalesforceReonomy's first ownership-data integration needed a thin API layer, a property ID, and a useful object inside the customer's CRM.
  73. 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.
  74. No Email, Lots of BrickA nearly offline weekend in Indiana opened up a doorway and moved my childhood-home rebuild into a much more visible phase.
  75. 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.
  76. Indiana With a HammerAnother trip to my childhood home meant plumbing, carpentry, and the slow move from demolition into rebuilding.
  77. 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.
  78. A Hundred Hours InRoughly 100 hours of early Reonomy work were enough to make me want to give the company my full attention.
  79. Training Fell ApartGetting sick, closing on a condo, and interviewing for a new job pushed training out of my schedule.
  80. The Loft Was MineAn ID, a checkbook, and one final confirmation were all that remained before the purchase at 60 Broadway closed.
  81. 104 PagesTwo bank transfers turned into a 104-page mortgage document package while the purchase at 60 Broadway was still waiting on underwriting.
  82. Forty-Five DaysThe mortgage deadline arrived during Christmas week, the banker was away, and the 60 Broadway deal could still fall apart.
  83. In ContractAfter weeks of open houses and paperwork, the loft at 60 Broadway was officially becoming mine.
  84. Too Many Open HousesThe apartment search moved from one possible DUMBO offer to a Saturday route through several Brooklyn buildings.
  85. All Moved InA four-line email from March 2013 records a fast move into a new place and the end of a longer apartment search.
  86. Wear Flexible ClothingAmanda and I hosted Thanksgiving in Williamsburg with a turkey, pumpkin pies, bikes, board games, and optional head-dresses.
  87. Slept on the FloorThe Williamsburg loft had boxes, a real kitchen, a king bed on the way, and one very happy new tenant.
  88. Williamsburg, PleaseThe apartment search narrowed to a small loft with high ceilings, big windows, and a January move.
  89. Four Pieces, One LoftThe Lower East Side apartment needed a couch, a TV stand, and exactly two dressers.
  90. Few Months LateSpring cleaning reached the New York apartment in June, complete with new shelves, a whiteboard wall, and a lot of shoes.
  91. 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.
  92. The Rad PillowAfter the U-Haul, the filthy apartment, and a couch that barely fit, one homemade pillow made the place look like ours.
  93. Almost to IndianaWe were driving our belongings east while Peek was already asking me to price a data center and route traffic back to Amazon.
  94. Permanently, Last WeekI had finally moved to New York, changed my phone number, and still answered the recruiter calling about another infrastructure job.
  95. Last Tickets to DenverThe final Denver flights and a one-way U-Haul turned the New York move into something we could no longer treat as a plan.
  96. The U-Haul Was $1,100Yodle wanted references, which made the job feel real enough to price a moving truck and a trailer for the Jeep.
  97. My Third JobBeatport, two consulting jobs, and a phone photo sent with one blunt explanation: I wanted a loft.
  98. February TenthA small Denver studio was approved far enough for a lease, and I accepted a proposed February 10 move-in date.
  99. The Apartment Called About the DogA Cherry Creek property manager asked me to call immediately about my dog.