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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97 stories / Cycling. 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. Katonah on Two WheelsNeutral Ground came back to Katonah for a fourth year of road routes, gravel, and a cycling expo afterward.
  3. The KICKR Went QuietAn indoor trainer connected normally but stopped broadcasting power data.
  4. Both Bikes, NaturallyA February maintenance note covered a new bike build, an older road bike, shifting, the drivetrain, and a saddle swap.
  5. Not Quite There YetI signed off on Loop's first Alpha, wrote down exactly what still did not work, and asked my running club to help me find a React Native engineer.
  6. Good Week, Weird WeekWe signed Loop's term sheet, I went to LA Tech Week for fundraising, celebrated at home and on a bike, and finished with another investor no.
  7. The Pitch and Run I MissedA flat city-bike tire made me miss an investor run while Loop was still asking people to bet on an Alpha they could not test.
  8. Thirteen Before LunchI ran 13.6 hilly miles through the Hudson Valley, then got on the bike for another 48.2.
  9. Over 300 Up BearSix days after my derailleur went into the spokes, I returned to Bear Mountain and set two climbing PRs.
  10. Eight Weeks, Then LoopI left a new full-time CPTO job at Pinata to cofound Loop and start building an AI professional-networking product from scratch.
  11. My Ramen Got ColdA month into my New York job search, interviews, closets, dog-sitting, and a bike rebuild had filled every supposedly free day.
  12. By the End of Q1I moved back to New York, started a serious job search, and gave myself one quarter to find the next product and technology role.
  13. The Test Said Zone 2A Boston lab put numbers on my plan to get back into racing shape, including a 275-watt FTP, limited mobility, and a lot more easy work.
  14. Can You Limp to Worlds?A bad ankle turned the USA Triathlon Long Course Duathlon National Championship into a half-marathon limp, but the Team USA spot survived.
  15. The Whole Bike Came Down to a ClampA missing seatpost clamp turned my older Pinarello Montello FM1 and an approaching Florida race into a search for one obsolete piece of metal.
  16. Not Bored Enough for the Wrong ThingAfter the cross-country ride and an overseas trip, I came back to New York, finished an Apply handoff, moved into Rockaway, and started looking for the right next project.
  17. The Bike Boom EndedWahoo closed RGT on October 31, 2023 after a difficult period for connected fitness and the indoor cycling market.
  18. We BackThree riders came home after 29 days, 13 states, 3,000 miles, 25 flats, two falls, and no days off.
  19. The Last StateNew Jersey was the last state before home, which meant one more day of bad jokes, tired legs, and getting the bikes to New York.
  20. The First RainWe crossed the Mississippi, found an Illinois rail trail, and finally got properly wet at the Wabash Cannonball Bridge.
  21. Arkansas Gets One PostTwo days in Arkansas included hay, rolling roads, attack dogs, an armadiller, night riding, and one combined update from Missouri.
  22. The SAG AwardBig Ted drove the little MINI, made the sandwiches, and kept our rolling circus moving across Texas and Oklahoma.
  23. Dead Biker PassNew Mexico gave us art, hot springs, Taos, the Rockies, and a road sign with an aggressively specific warning.
  24. America's Greatest Bike TrailArizona gave us red rocks, rough roads, Winslow, the Continental Divide, and a 75-mile-an-hour bicycle trail called Interstate 40.
  25. We Don't Talk About Day 5The first five days brought desert heat, strangers, Route 66, a night ride, and enough mechanical trouble to earn one very short update.
  26. 2,913 Miles to GoWe left the Pacific in Santa Monica with two bikes, one very long route, and most of the country still in front of us.
  27. The Bike Was Still in the OfficeI exited Wahoo, asked for a few extra days of badge access to retrieve my bike, and started recruiting support for a ride across the United States.
  28. Where Did the Shoe Go?A hard turn on a descent tore the cleat plate out of a cycling shoe and left the cleat attached to the pedal.
  29. How Many Bikes Fit?An early River Road personal best ended at a Piermont deck where bicycles outnumbered chairs and number 1,426 still counted.
  30. My Job Moved FirstWahoo wanted my role in Atlanta, so a two-week stretch began with H2 planning, canceled meetings, and an indoor bike because it was 91 degrees.
  31. Simplifying, ApparentlyA Rockaway closing, a cash offer in Cornwall, two Highland land plots, and one small balcony went into the same July spreadsheet.
  32. I Missed the ContractThe Rockaway closing packet had contracts, riders, disclosures, wire instructions, and one completely unsigned contract.
  33. The Fire Pit StaysA verbal Rockaway offer came with nine patio items, one mortgage contingency, and a spreadsheet for what stayed.
  34. I Need GitHub AccessA one-line access request put Wahoo's code repositories, my existing GitHub account, and a very Wahoo workstation in the same afternoon.
  35. Can We Enable AirPlay?NYC Marathon weekend ran straight into an Atlanta Wahoo trip, two Apple TVs, SYSTM testing, group rides, and an indoor invitation back in Manhattan.
  36. Both Screens OnWahoo X launch week moved from a team note and bundle copy to RGT on the television and SYSTM on a tablet at home.
  37. Not Much of a BedroomA new KICKR turned one corner of the New York apartment into the place for early rides before work.
  38. Lewis and Clark AdventureA Saturday ride found train tracks, mud, lily pads, and a route that made more sense after Strava drew the line.
  39. I'm on PTOA Colorado trip with Amanda and Eva still found room for Wahoo's new sports science center, an all-black logo, and cheap pizza.
  40. This Week Is a Little NutsA first real Atlanta work trip landed between product teardowns, Apply reports, a hot long-run idea, and another bike problem.
  41. Achievement UnlockedWeek two at Wahoo mixed subscription and running-product work with a stuck Apply marketplace integration and plans to crew the Leadville 100.
  42. 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.
  43. 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.
  44. Soon to Be an Official WahooliganI signed the Wahoo agreement, then went straight back into RGT to build a route, find its riders, and test the no-drop feature.
  45. Potentially Bringing a BikeA Wahoo visit in Atlanta collided with a house purchase in Cornwall, Apply work, and one very important packing question.
  46. 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.
  47. Cycling Cycling CyclingTesting power pedals and Wahoo SYSTM made the product questions inside an active Wahoo interview process much less theoretical.
  48. Thread the NeedleA TRX work week in California ran directly into two days of Wahoo interviews in Atlanta, with one narrow travel handoff between them.
  49. 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.
  50. The Peugeot Got WeirdAn old steel Peugeot frame, a modern one-by drivetrain, and two sets of pedals became my January bike project.
  51. Pumped to Meet YaApply hired somebody to own fulfillment just as a 45-order weekend hit, while TRX builds and the Newport Beach commute kept moving.
  52. A Solid Race, Then SpamThe long-course bike leg was honest about my preparation. The next start line depended on recovering a registration email from spam.
  53. The Bike Came TooA work apartment in Newport Beach needed lights and furniture, but I unpacked the race bike and put it on a trainer first.
  54. Is There a Red Kit?USA Triathlon made my All-American status official, and I spent four emails trying to find out whether a national champion kit came with it.
  55. 10.0.7 to 10.0.10Four TRX app versions moved through Apple while I flew from New York to Newport Beach, sorted product details, and tried to keep one foot in Apply.
  56. I Won NationalsI finished the sprint duathlon in 1:05:58 and won the men's 35–39 draft-legal national title in Tuscaloosa.
  57. I Picked a Bad MorningElection stress sent me out for a Thursday bike ride. A few hours later I was in the ER, apologizing in advance for concussion typos.
  58. A Pretty Big LiftI had wanted to ride across America for years. COVID turned the supported version into a much stranger solo plan.
  59. 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.
  60. The Training Sheet Just StopsA 2020 race plan recorded illness, a sore Achilles, and several target races before the schedule stopped during COVID.
  61. Twenty-One, Then WorkThe New York City Marathon became a 21-mile training run. I paced a struggling friend, stopped before the finish, and kept the next workweek intact.
  62. No Worlds. Maybe Fifty Miles.A healing foot took the duathlon world championship away, while I tried to make a 50-mile qualifier sound like the sensible alternative.
  63. Sixty PercentMy first run after the NYC Half lasted 30 minutes on an Alter-G treadmill at 60 percent body weight.
  64. The Race Stayed in BedI asked how hard to ride Staten Island's 20K bike, then decided at 5:45 a.m. that staying in bed was the better plan.
  65. The Race I Blew, We WonA bad five-miler in 97 percent humidity became a team championship, then forced a harder question about work stress, a sick friend, and what the body carries.
  66. Second Fastest, Still TrainingA 17:56 5K landed in the middle of a heavy run-and-bike block, complete with tired legs, bad fueling, and a map of the miles it took just to leave New York.
  67. Second by Four SecondsI had the fastest bike split at the Tri One On duathlon, then ran an extra 300 meters and missed the overall win by four seconds.
  68. I Nearly Melted DownA month of 12-to-14-hour startup days left me exhausted and injured, even while I ran a marathon qualifier and a 17:45 road 5K.
  69. The Thirty-Minute Coaching CallA call with world champion triathlete Lesley Paterson became both a real attempt to improve my duathlon training and a premium-coaching product example for Aaptiv.
  70. 375 Miles, Then the PlaneSeven days at Trek Travel's South Carolina Ride Camp put 375 cycling miles and 20 running miles into my legs. The flight home was the part that caused trouble.
  71. Fourth, Then Team USAI finished fourth in my age group at the national draft-legal sprint duathlon and earned a Team USA slot.
  72. Good Idea or Crutch?A slow-healing calf took the Snickers Marathon off my calendar. I had a pair of inserts, a bike, and a new half-marathon target.
  73. Do I Buy Two Bibs?Running both Cocoa Classic distances was the plan until snow converted the races, just as a 50-mile training plan arrived.
  74. Nowhere Near EitherI wanted a sub-17 5K and a sub-2:54 marathon. My current times, irregular schedule, and old training calendar showed the gap.
  75. Better Than the SubwayAt Aaptiv, I could run or bike to the office, train with coworkers, and work on a fitness product I used myself.
  76. 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.
  77. The Result Was WrongMy race-day email said 41:15 and sixth place. The official result said 41:47 and tenth, and my left leg still needed a doctor.
  78. The Battery Door BrokeA broken battery door put my Stages power meter out of service until a replacement cover and O-rings arrived.
  79. Take the Cassette ApartI signed up to learn bicycle maintenance, pulled apart a rear wheel, and ended the day debugging a power-meter update.
  80. 44:04Forty-four minutes and four seconds put a number on my PPTC Al Goldstein Summer Speed Series 5K finish, with an early cycling slot two days later.
  81. 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.
  82. I Feel Fucking GreatI resigned from Reonomy, accepted Aaptiv's CTO and VP Product role, and started learning the mobile stack before my first day.
  83. Same Flights, Same CampA group of friends booked a week of road riding in South Carolina, giving the spring training calendar a real shape.
  84. Placid Was OutThe back injury made an Ironman at Lake Placid unrealistic, so I asked to transfer the entry and considered going only to cheer.
  85. So Fucked for PlacidLake Placid was getting close while work, moving, and training were all fighting for the same hours.
  86. Qualified. Bad Timing.Nation's Triathlon put me into the national championships. The race landed two weeks after my Ironman.
  87. Sea to SeaEight days across the Pyrenees changed what I thought a bike trip and my own legs could handle.
  88. Forgot My ShoesWest Point was a two-minute PR with a better swim, a stiff back, tired legs, and bike shoes left in transition.
  89. Let's Dream a LittleThe next twelve months included faster road races, a long swim, another Ironman, and a bike trip across the Pyrenees.
  90. Jellyfish and a DecadeThe Cozumel swim had current, jellyfish, and plenty of people who did not finish. I stayed calm and completed the goal.
  91. Wear Flexible ClothingAmanda and I hosted Thanksgiving in Williamsburg with a turkey, pumpkin pies, bikes, board games, and optional head-dresses.
  92. Yes, I Would Like to ParticipateSecond in my age group at Westchester came with a slot for Escape from Alcatraz. The answer was immediate.
  93. Painless. A Little Clumsy.The first run after a hard race did not hurt. That was enough good news to keep the week moving.
  94. Here's the DealioThe Ironman plan was a beach, a Sunday race, a ferry, and the hardest physical thing I had ever tried.
  95. Broke a PedalSeven miles into a triathlon, the pedal broke. The transitions were bad too. I finished anyway.
  96. Ride to Work. Run Leadville?I was biking to work, training for a difficult marathon, and considering the Leadville Trail 100 run.
  97. Someone Forgot the DomainA BMX forum disappeared behind an advertising page when its domain expired, then returned after the operator renewed it.