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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130 stories / Running. 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. 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.
  3. 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.
  4. Ten Miles, 60:53I ran 60:53 at the 2024 South Nyack 10-Miler, finished ninth overall, and won the men's 40–44 age group.
  5. Thirteen Before LunchI ran 13.6 hilly miles through the Hudson Valley, then got on the bike for another 48.2.
  6. Thirty-Three Hours, Three LegsA 12-person Wild West Relay team ran 200 miles from Fort Collins to Steamboat Springs while I covered three legs and 19.7 miles across Colorado.
  7. 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.
  8. 18:44 in McCarrenI ran 18:44.86 at the 2024 Dime McCarren 5K and finished second in the men's 40–49 age group.
  9. We Agreed Not to RaceThree of us started the NYCRUNS Brooklyn Half with a no-drop plan. It became the most fun I had ever had in a race.
  10. The Couch Finally ArrivedRockaway finally had a real couch, a pullout bed, and one less reason to call the condo unfinished.
  11. So Silly to Say Out LoudA scooter accident tore my rotator cuff just as two final interview tracks and the USOPC search reached decision week.
  12. 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.
  13. 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.
  14. Does Thanksgiving Need a Couch?The Rockaway condo was still half moved-in, but Thanksgiving was coming anyway.
  15. 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.
  16. Simplifying, ApparentlyA Rockaway closing, a cash offer in Cornwall, two Highland land plots, and one small balcony went into the same July spreadsheet.
  17. A Kind Man in BlackA 17:24 5K, a 2:59 Boston Marathon, and the last 800 meters I did not expect to run with somebody else.
  18. What Is That Ruin?A run to the south end of Roosevelt Island stopped at the roofless Smallpox Hospital beside the East River.
  19. The Time Zone ChangeAn unexpected family week, Wahoo user research, and a long-planned trip to Switzerland all met in the same inbox.
  20. 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.
  21. Fifth, Then FirstI ran a half marathon PR, handed the CIM relay to Ted in fifth, and watched him bring us home first out of 418 teams.
  22. 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.
  23. 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.
  24. Achievement UnlockedWeek two at Wahoo mixed subscription and running-product work with a stuck Apply marketplace integration and plans to crew the Leadville 100.
  25. Potentially Bringing a BikeA Wahoo visit in Atlanta collided with a house purchase in Cornwall, Apply work, and one very important packing question.
  26. One Twenty, Then Strategy DayAmanda and I ran New Orleans, then Apply went straight back to museums, licensing reports, and a Friday strategy day at WeWork.
  27. The Peugeot Got WeirdAn old steel Peugeot frame, a modern one-by drivetrain, and two sets of pedals became my January bike project.
  28. It Is Not ITTRX and Apply were in their holiday push when a restaurant concept asked me to help define and vet its first real technology leader.
  29. The Crew Side of the CourseA Javelina race weekend began with last-minute errands and became a long day among tents, cactus hills, and waiting.
  30. Forget the TimeAt the 2021 Chicago Marathon, I changed my goal and stayed with a teammate who was having a hard day.
  31. 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.
  32. 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.
  33. Wonky MarathonsPPTC's marathon group came back with three mileage plans, Discord channels, virtual office hours, and no official group runs.
  34. I Won NationalsI finished the sprint duathlon in 1:05:58 and won the men's 35–39 draft-legal national title in Tuscaloosa.
  35. 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.
  36. 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.
  37. Thirty Minutes BeforeI broke my hand on a trail run half an hour before a TRX conversation, then had to ask how the workout product handled one usable hand.
  38. 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.
  39. Tempted (Joking)A wholesale coordinator job at the Poughkeepsie Farm Project landed in my inbox while I was building Apply. The joke was that I might want it. I sort of did.
  40. No D1 Athletes From TexasThe Plague Games turned four canceled-race months into track time trials with GPS proof, tiny groups, pizza, and very specific anti-stacking rules.
  41. Aaptiv, From HomeAaptiv's at-home fitness use jumped, and the company opened a new enterprise and API channel.
  42. The Training Sheet Just StopsA 2020 race plan recorded illness, a sore Achilles, and several target races before the schedule stopped during COVID.
  43. Every Rep Leaned LeftA 16-by-400 workout looked fast and consistent, but every repeat showed the same small pacing mistake.
  44. Two Broken TreadmillsA messy California International Marathon taper ended with a handmade 2:47:30 pace band and a 2:47:55 finish.
  45. 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.
  46. Nobody Feels PerfectThe night before the Chicago Marathon, I was calming down the runners I coached while rebuilding my own fitness after six weeks in a boot.
  47. Nine Out of TenA recruiter suggested I talk to a venture firm. I explained the unfinished degree, years inside startups, and why most firms might still say no.
  48. 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.
  49. The MRI Voted NoThe MRI found a chronic partial tear in my right forefoot, so I deferred Berlin, got a boot, and asked if swimming still counted.
  50. Finish, Not TimeThe Vermont 100 was crazy hot. I stopped chasing the clock, finished in 27:13, and went back to writing Tuesday's workout.
  51. 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.
  52. One Hundred Eighty-SevenThe PPTC Marathon Training Group had 187 runners, one volunteer coaching crew, and a lot of TrainingPeaks accounts to load.
  53. Two Forty-Five, PleaseI bought a marathon plan from Brad Hudson, marked it up, then brought the questions straight into Aaptiv.
  54. No Tricks. No Shortcuts.We built a twelve-week Aaptiv running plan with base miles, hills, tempo work, long runs, recovery, and a taper before race day.
  55. A Party With Long RunsI joined PPTC's 2019 marathon training group as a coach and found a signup list with a lot of different times and experience.
  56. The Foot Did ThirteenLess than six weeks after my first Alter-G run, the Brooklyn Half put 13.3 GPS miles on the foot that had stopped my spring.
  57. Chili, Recovery Socks, Hair MetalRock The Ridge started as a completely unreasonable podium attempt and became 50 excellent miles of bad math, aid-station chili and survival.
  58. 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.
  59. Sixty PercentMy first run after the NYC Half lasted 30 minutes on an Alter-G treadmill at 60 percent body weight.
  60. The Book Was Too BigI finished the RRCA coaching course in Poughkeepsie, then immediately asked if the giant manual came in an iPad version.
  61. One Eighteen, Blown FootI ran 1:18:23 at the 2019 New York City Half, hit the time I wanted, and wrecked my right foot doing it.
  62. Three Out of FourI ran for the Prospect Park Track Club board with a phone-typed pitch for our great, wild and weird club.
  63. Thirty-One Miles, Then EvaI ran a low-key 50K with friends as early training for two ultras, then recovered on the couch with Eva.
  64. Stop NoahOur Cherry Tree relay team ran 54:44 in Prospect Park. My leg averaged 5:29 and gave me the 17:01 I had been looking for.
  65. It Needed Two HandsProspect Park Track Club won the NYRR Open Men B division, so twenty of us put on suits and collected a very large glass trophy.
  66. 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.
  67. Dingleberry Was My Favorite WordAmanda and I brought party rollups to Harry's Handicap, where start times were staggered and the potluck included a contest for the best word.
  68. Fifty-Four Fifty-ThreeA cold Ted Corbitt 15K put me on the PPTC record list, then the week went straight back to club runs and volunteer points.
  69. Course Map, IshA Zipcar, a guessed-at Strava route, and a muddy 10K with the Prospect Park Track Club crew.
  70. Five Miles, Not Twenty-FiveA bitter-cold forecast had runners dropping from five miles to two. I asked about moving up to 25K, stayed in the five, and ran 30:42.
  71. Three Minutes to SpareI needed 2:59:59 in my first New York City Marathon. I finished in 2:56:51, twenty seconds slower than Chicago and safely under the line.
  72. GAP at SixI went looking for three winter running partners at Grand Army Plaza and accidentally found a group.
  73. Two Fifty-Six and an Ice BathI ran 2:56:31 at the 2018 Chicago Marathon, then sat in a hotel bathtub trying to get my legs back.
  74. No Day Pass. Still Ran.A Paris gym would not sell me a day pass, so I found a 400-meter track and ran five mile repeats while keeping an eye on a sore foot.
  75. 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.
  76. 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.
  77. The Bib Arrived EarlyI thought my Brooklyn Half time was for 2019. Prospect Park Track Club found me a 2018 New York City Marathon bib instead.
  78. Twenty-Eight Miles, Fifteen PoundsI carried a fifteen-pound pack through a wet 28-mile Catskills weekend with 6,500 feet of climbing.
  79. 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.
  80. 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.
  81. 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.
  82. Twenty-Two Million, Then the WoodsAaptiv's Series C was public. I carried 35 pounds into Echo Lake, ran a ridge in absurd rain, and got the mental escape I needed.
  83. 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.
  84. 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.
  85. My Laptop Ran the 5KI jogged to the Al Goldstein 5K carrying work clothes and a laptop, then looked back at the year that made running feel like a team sport again.
  86. The Leg HeldA questionable leg, a borrowed bib pickup, cold rain, and a 1:20:44 Brooklyn Half that put me under the New York City Marathon time standard.
  87. 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.
  88. 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.
  89. Fourth, Then Team USAI finished fourth in my age group at the national draft-legal sprint duathlon and earned a Team USA slot.
  90. One Hundred Twenty EggsI bought 120 eggs and hosted the dyeing crew for Prospect Park Track Club's Easter egg hunt.
  91. 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.
  92. Run, Eat, Drink, OrganizeThree months after joining PPTC, I moved from morning and weekend group runs onto the club's Social Committee.
  93. Nine in the Storm, Seven AfterI ran nine miles during New York's bomb cyclone, then went back out at 6:00 the next morning for seven more.
  94. 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.
  95. 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.
  96. Find a Workout, Miss a RaceI wrote five ways to get new Aaptiv members into a first class while working late kept me out of the OSR10K.
  97. 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.
  98. 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.
  99. 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.
  100. Five Twenty-NineI ran 5:29 at the New Balance Fifth Avenue Mile, less than two months after my first 5K back.
  101. Twenty Forty-FiveFive months after a stress fracture put running on hold, I raced a Prospect Park 5K in 20:45.
  102. 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.
  103. 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.
  104. 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.
  105. What Do I Do Today?While I was considering a role at Aaptiv, I tried the workouts and wrote Ethan about navigation, training plans, class data, and recommendations.
  106. Twelve Miles to a 5KAmanda and I registered for a Thanksgiving 5K in Colorado Springs after confirming the race was only about twelve miles away.
  107. Run Club Ran LongA 4.54-mile company run down the West Side turned into snacks, drinks, and a much longer evening than planned.
  108. Run Gear Was a Bad CallI rushed into a meeting dressed to run, got called on it, and stopped defending my own standard for punctuality.
  109. 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.
  110. So Fucked for PlacidLake Placid was getting close while work, moving, and training were all fighting for the same hours.
  111. Training Fell ApartGetting sick, closing on a condo, and interviewing for a new job pushed training out of my schedule.
  112. Qualified. Bad Timing.Nation's Triathlon put me into the national championships. The race landed two weeks after my Ironman.
  113. Coughing After PhillyA bad chest cold took out the last training days. I still ran 1:26, then went looking for pancakes.
  114. One Point One Miles UpStorm King was seven and a half miles, one long hill, eighth overall, and exactly the kind of hard race I liked.
  115. Two Pilsners. One PR.A North Brooklyn Runners team night produced my fastest 10K in twelve years and a questionable pre-race nutrition theory.
  116. Forgot My ShoesWest Point was a two-minute PR with a better swim, a stiff back, tired legs, and bike shoes left in transition.
  117. Let's Dream a LittleThe next twelve months included faster road races, a long swim, another Ironman, and a bike trip across the Pyrenees.
  118. Apparently I Wanted EverythingA few weeks after Shutterstock went public, I planned a marathon, two half Ironmans, Leadville, a long swim, and several time goals for 2013.
  119. Jellyfish and a DecadeThe Cozumel swim had current, jellyfish, and plenty of people who did not finish. I stayed calm and completed the goal.
  120. Yes, I Would Like to ParticipateSecond in my age group at Westchester came with a slot for Escape from Alcatraz. The answer was immediate.
  121. Painless. A Little Clumsy.The first run after a hard race did not hurt. That was enough good news to keep the week moving.
  122. I AcceptNorth Brooklyn Runners had no dues, a long code of ethics, and coffee after the Williamsburg Bridge run.
  123. Here's the DealioThe Ironman plan was a beach, a Sunday race, a ferry, and the hardest physical thing I had ever tried.
  124. Broke a PedalSeven miles into a triathlon, the pedal broke. The transitions were bad too. I finished anyway.
  125. Joined the GymRetro Fitness followed up about a free day pass. The answer was shorter: I had already joined.
  126. I Signed You UpLeadville was high, hard, and apparently something I had decided somebody else should do with me.
  127. Yep, Sounds GoodA Mudder spot opened, the payment could transfer, and my entire decision took three words.
  128. Nike+ at the GymA 24 Hour Fitness email passed along a Finish Line offer for the Nike+iPod running kit.
  129. Five Hours Was OptimisticI finished the 2006 Leadville Trail Marathon in 5:37:50, 74th out of 238 finishers.
  130. Ride to Work. Run Leadville?I was biking to work, training for a difficult marathon, and considering the Leadville Trail 100 run.