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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66 stories / Travel. Newest first.

  1. Katonah on Two WheelsNeutral Ground came back to Katonah for a fourth year of road routes, gravel, and a cycling expo afterward.
  2. The Car Grew a RoofI replaced the closed carrier on my Mini with an open cargo cage, then immediately started planning what could go on top of it.
  3. Ninety-Four Floors UpA short Chicago weekend moved from the Adler Planetarium to sunset drinks above Lake Michigan.
  4. We BackThree riders came home after 29 days, 13 states, 3,000 miles, 25 flats, two falls, and no days off.
  5. 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.
  6. The First RainWe crossed the Mississippi, found an Illinois rail trail, and finally got properly wet at the Wabash Cannonball Bridge.
  7. Arkansas Gets One PostTwo days in Arkansas included hay, rolling roads, attack dogs, an armadiller, night riding, and one combined update from Missouri.
  8. The SAG AwardBig Ted drove the little MINI, made the sandwiches, and kept our rolling circus moving across Texas and Oklahoma.
  9. Dead Biker PassNew Mexico gave us art, hot springs, Taos, the Rockies, and a road sign with an aggressively specific warning.
  10. 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.
  11. 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.
  12. 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.
  13. 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.
  14. Thanks for the Reserve PoursA west-coast vacation produced a winery photo, two PEJU receipts, and one thank-you note for the extra tasting.
  15. Simplifying, ApparentlyA Rockaway closing, a cash offer in Cornwall, two Highland land plots, and one small balcony went into the same July spreadsheet.
  16. The Fire Pit StaysA verbal Rockaway offer came with nine patio items, one mortgage contingency, and a spreadsheet for what stayed.
  17. How Long Until Zillow?A two-night Rockaway Beach weekend turned into open houses, neighborhood research, and a 70-page park plan.
  18. Which Part Was the Art?A free Sunday at the Getty Center left three photos, all of Robert Irwin's Central Garden and none from inside the galleries.
  19. Mom Gets the DaySanta Monica moved Apply cofounder work to 7 a.m. Pacific and pushed a Wahoo standup aside for Gisi's birthday.
  20. The Time Zone ChangeAn unexpected family week, Wahoo user research, and a long-planned trip to Switzerland all met in the same inbox.
  21. Napa, Then Back to the GrindA five-person wine tasting at Turnbull turned one Monday in California into a short Napa itinerary.
  22. A Little BreakAmanda's birthday and our ten-year anniversary took us to Cusco and Machu Picchu after a week of Wahoo travel and Apply work.
  23. 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.
  24. 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.
  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. 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.
  27. 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.
  28. 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.
  29. 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.
  30. 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.
  31. 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.
  32. 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.
  33. 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.
  34. Twenty-Eight Miles, Fifteen PoundsI carried a fifteen-pound pack through a wet 28-mile Catskills weekend with 6,500 feet of climbing.
  35. 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.
  36. Odd Hours in IcelandFour nights, four stops, two South Coast routes, and a work call I was still trying to coordinate from Iceland.
  37. My Cell Worked InternationallyAmanda and I moved through Berlin, Prague, and Warsaw while Aaptiv hiring and a half-renovated Poughkeepsie house kept reaching me.
  38. Find Bus OneAmanda and I went to Washington with friends for the Women's March, then spent the evening getting four people off a delayed Metro and back to Bus One.
  39. The Gear Was GoneA Catskills camping weekend ended with a stolen phone, tent, sleeping bag, and the start of replacing what had disappeared.
  40. Morning, Twilight, MorningA Cozumel dive weekend had one simple rhythm, plus a night dive that never fit neatly into the schedule.
  41. Still OutsideA Catskills backpacking return and an all-day Habitat for Humanity shift kept the week's plans moving around.
  42. Same Flights, Same CampA group of friends booked a week of road riding in South Carolina, giving the spring training calendar a real shape.
  43. 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.
  44. 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.
  45. 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.
  46. Sea to SeaEight days across the Pyrenees changed what I thought a bike trip and my own legs could handle.
  47. Eva Goes to DCThe race trip had one harder logistics problem than the bike: getting Eva there and home without making Sunday worse.
  48. The Pool Part Was NextI completed the six online sections of the PADI Open Water course, with the real pool and open-water work still ahead.
  49. Book the RoomIronman Cozumel was six weeks away. Amanda and I still needed somewhere to sleep after it.
  50. Here's the DealioThe Ironman plan was a beach, a Sunday race, a ferry, and the hardest physical thing I had ever tried.
  51. Calling From a Wine CellarA monitoring demo followed me from San Francisco to the mountains to Napa, where the only honest location update was the wine cellar.
  52. I Signed You UpLeadville was high, hard, and apparently something I had decided somebody else should do with me.
  53. 60K in a FieldTwo nights after watching the Netherlands reach the World Cup final in Amsterdam, I sent one good photo from the trip.
  54. 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.
  55. The 12:55 A.M. FlightOne overnight flight could get me from Denver to a New Jersey startup interview, if I could find the money and stay awake.
  56. Two Canceled FlightsNew York interviews went well, but two canceled flights kept me there while Denver consulting work waited.
  57. The 1977 CJ5I proposed taking Greyhound to inspect a yellow 1977 Jeep in Grand Junction, and two days later I owned it.
  58. Ski Season in JulyVail Resorts asked about my ski-vacation preferences in the middle of a Denver summer, two months after pitching the new Epic Pass.
  59. Royal Gorge, MaybeA June group email tried to organize a camping and whitewater rafting weekend at Colorado's Royal Gorge.
  60. The Beach at A-BasinMemorial Day plans called for a 12-person tent, soft snow, a grill, beer, and one more day of skiing at Arapahoe Basin.
  61. Zero PEAKS PointsMy ski account ended the 2007–08 Colorado season with no reward points and a $579 Epic Pass offer.
  62. Dogs Allowed or No DealSearching for an August weekend in Estes Park came down to one requirement: the puppy had to be allowed.
  63. Chicago for a WeddingThe itinerary and my photos line up: I flew from Denver to Chicago for a wedding weekend in May 2006.
  64. Chicago Was on the CalendarI booked a May trip from Denver to Chicago and filed the confirmation with the rest of the travel mail in my new Gmail account.
  65. Italy Blocked EverythingA network in Italy allowed web traffic but blocked the VPN, SSH, remote desktop, and dial-out access I needed for work.
  66. Gmail, Denver, DoneA new Gmail account handled a Denver flight, a friend's invitation, and the same mail tests I was still running against SimAuthor.