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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74 stories / Racing. Newest first.

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
  12. Wonky MarathonsPPTC's marathon group came back with three mileage plans, Discord channels, virtual office hours, and no official group runs.
  13. I Won NationalsI finished the sprint duathlon in 1:05:58 and won the men's 35–39 draft-legal national title in Tuscaloosa.
  14. 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.
  15. 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.
  16. The Training Sheet Just StopsA 2020 race plan recorded illness, a sore Achilles, and several target races before the schedule stopped during COVID.
  17. Two Broken TreadmillsA messy California International Marathon taper ended with a handmade 2:47:30 pace band and a 2:47:55 finish.
  18. 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.
  19. 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.
  20. 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.
  21. One Hundred Eighty-SevenThe PPTC Marathon Training Group had 187 runners, one volunteer coaching crew, and a lot of TrainingPeaks accounts to load.
  22. Two Forty-Five, PleaseI bought a marathon plan from Brad Hudson, marked it up, then brought the questions straight into Aaptiv.
  23. 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.
  24. 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.
  25. 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.
  26. 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.
  27. 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.
  28. 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.
  29. 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.
  30. 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.
  31. 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.
  32. 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.
  33. 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.
  34. 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.
  35. 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.
  36. 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.
  37. 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.
  38. 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.
  39. 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.
  40. 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.
  41. 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.
  42. 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.
  43. 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.
  44. 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.
  45. 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.
  46. 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.
  47. 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.
  48. Fourth, Then Team USAI finished fourth in my age group at the national draft-legal sprint duathlon and earned a Team USA slot.
  49. 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.
  50. 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.
  51. Five Twenty-NineI ran 5:29 at the New Balance Fifth Avenue Mile, less than two months after my first 5K back.
  52. 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.
  53. CTO, Ironman FinisherA short 2015 bio tried to fit startup leadership, Shutterstock's IPO years, Reonomy, and endurance sport into one paragraph.
  54. 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.
  55. So Fucked for PlacidLake Placid was getting close while work, moving, and training were all fighting for the same hours.
  56. Training Fell ApartGetting sick, closing on a condo, and interviewing for a new job pushed training out of my schedule.
  57. Qualified. Bad Timing.Nation's Triathlon put me into the national championships. The race landed two weeks after my Ironman.
  58. Coughing After PhillyA bad chest cold took out the last training days. I still ran 1:26, then went looking for pancakes.
  59. 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.
  60. Eva Goes to DCThe race trip had one harder logistics problem than the bike: getting Eva there and home without making Sunday worse.
  61. Forgot My ShoesWest Point was a two-minute PR with a better swim, a stiff back, tired legs, and bike shoes left in transition.
  62. Let's Dream a LittleThe next twelve months included faster road races, a long swim, another Ironman, and a bike trip across the Pyrenees.
  63. 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.
  64. Jellyfish and a DecadeThe Cozumel swim had current, jellyfish, and plenty of people who did not finish. I stayed calm and completed the goal.
  65. Yes, I Would Like to ParticipateSecond in my age group at Westchester came with a slot for Escape from Alcatraz. The answer was immediate.
  66. Book the RoomIronman Cozumel was six weeks away. Amanda and I still needed somewhere to sleep after it.
  67. Painless. A Little Clumsy.The first run after a hard race did not hurt. That was enough good news to keep the week moving.
  68. Spend $350 to SwimI found a weekend freestyle clinic in New Paltz and invited a friend with a very honest sales pitch.
  69. Here's the DealioThe Ironman plan was a beach, a Sunday race, a ferry, and the hardest physical thing I had ever tried.
  70. Broke a PedalSeven miles into a triathlon, the pedal broke. The transitions were bad too. I finished anyway.
  71. Put Some Weight on ItFour guys, two teams, one spreadsheet, and a lifting bet to keep the 5/3/1 cycle honest.
  72. Yep, Sounds GoodA Mudder spot opened, the payment could transfer, and my entire decision took three words.
  73. Five Hours Was OptimisticI finished the 2006 Leadville Trail Marathon in 5:37:50, 74th out of 238 finishers.
  74. Ride to Work. Run Leadville?I was biking to work, training for a difficult marathon, and considering the Leadville Trail 100 run.