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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357 stories / Life & people. 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. Unofficial Means BetterAn informal meetup built around live Claude demos needed hosts, and my name ended up on the list.
  3. The KICKR Went QuietAn indoor trainer connected normally but stopped broadcasting power data.
  4. Fine, Another ComputerI ordered a Raspberry Pi 5, more parts than the little computer needed, and another project for the pile.
  5. Goodword Is LiveGoodword launched publicly after a year of building, several months of controlled beta work, and a lot of unfinished lists.
  6. Do Not Sort AirtableA routine list cleanup produced one blunt rule: do not edit imported Airtable records while the table is sorted.
  7. 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.
  8. 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.
  9. 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.
  10. Thirteen Before LunchI ran 13.6 hilly miles through the Hudson Valley, then got on the bike for another 48.2.
  11. Over 300 Up BearSix days after my derailleur went into the spokes, I returned to Bear Mountain and set two climbing PRs.
  12. 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.
  13. 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.
  14. 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.
  15. Can We Be Both?A cofounder conversation about Loop became a real negotiation over ownership, pay, Pinata, Amanda, and where we could build the company.
  16. 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.
  17. 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.
  18. I Signed ItNine days after telling people I would probably pass on Pinata, I accepted the Chief Product and Technology Officer role and signed the offer.
  19. Forty, Phoenix, and an OfferI turned 40, flew to Arizona to help Mom with Dad's estate, and negotiated a startup offer from the other side of the country.
  20. Ninety-Four Floors UpA short Chicago weekend moved from the Adler Planetarium to sunset drinks above Lake Michigan.
  21. 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.
  22. 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.
  23. 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.
  24. 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.
  25. 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.
  26. Does Thanksgiving Need a Couch?The Rockaway condo was still half moved-in, but Thanksgiving was coming anyway.
  27. 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.
  28. We BackThree riders came home after 29 days, 13 states, 3,000 miles, 25 flats, two falls, and no days off.
  29. 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.
  30. The First RainWe crossed the Mississippi, found an Illinois rail trail, and finally got properly wet at the Wabash Cannonball Bridge.
  31. Arkansas Gets One PostTwo days in Arkansas included hay, rolling roads, attack dogs, an armadiller, night riding, and one combined update from Missouri.
  32. The SAG AwardBig Ted drove the little MINI, made the sandwiches, and kept our rolling circus moving across Texas and Oklahoma.
  33. Dead Biker PassNew Mexico gave us art, hot springs, Taos, the Rockies, and a road sign with an aggressively specific warning.
  34. 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.
  35. 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.
  36. 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.
  37. 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.
  38. 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.
  39. Thanks for the Reserve PoursA west-coast vacation produced a winery photo, two PEJU receipts, and one thank-you note for the extra tasting.
  40. I Missed the ContractThe Rockaway closing packet had contracts, riders, disclosures, wire instructions, and one completely unsigned contract.
  41. The Fire Pit StaysA verbal Rockaway offer came with nine patio items, one mortgage contingency, and a spreadsheet for what stayed.
  42. How Long Until Zillow?A two-night Rockaway Beach weekend turned into open houses, neighborhood research, and a 70-page park plan.
  43. 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.
  44. Mom Gets the DaySanta Monica moved Apply cofounder work to 7 a.m. Pacific and pushed a Wahoo standup aside for Gisi's birthday.
  45. 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.
  46. 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.
  47. What Is That Ruin?A run to the south end of Roosevelt Island stopped at the roofless Smallpox Hospital beside the East River.
  48. Who Signed This?Banksy in New York put an unauthorized exhibition, a map of city works, and a room full of stencils at 378 Broadway.
  49. 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.
  50. The Time Zone ChangeAn unexpected family week, Wahoo user research, and a long-planned trip to Switzerland all met in the same inbox.
  51. The Vet NoteEva's vet note arrived while Wahoo, Apply, travel, and the first workweek of the year were all starting up again.
  52. 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.
  53. Napa, Then Back to the GrindA five-person wine tasting at Turnbull turned one Monday in California into a short Napa itinerary.
  54. 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.
  55. Thanksgiving Is Just a Lot of WorkThe turkey needed a brine, a wire rack, a plan, and more coordination than anything else on the Thanksgiving table.
  56. 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.
  57. 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.
  58. 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.
  59. Open the Next Line SheetApply launched a LACMA collaboration while museum wholesale, production files, and my new Wahoo job all kept moving in the same week.
  60. Not Much of a BedroomA new KICKR turned one corner of the New York apartment into the place for early rides before work.
  61. Lewis and Clark AdventureA Saturday ride found train tracks, mud, lily pads, and a route that made more sense after Strava drew the line.
  62. 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.
  63. 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.
  64. Achievement UnlockedWeek two at Wahoo mixed subscription and running-product work with a stuck Apply marketplace integration and plans to crew the Leadville 100.
  65. 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.
  66. 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.
  67. Launch. Chapter 11. One Year.TRX Training Club launched on June 8, 2021. One year later, the company announced Chapter 11. Both dates belong in the story.
  68. 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.
  69. 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.
  70. Potentially Bringing a BikeA Wahoo visit in Atlanta collided with a house purchase in Cornwall, Apply work, and one very important packing question.
  71. Cycling Cycling CyclingTesting power pedals and Wahoo SYSTM made the product questions inside an active Wahoo interview process much less theoretical.
  72. 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.
  73. 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.
  74. 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.
  75. 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.
  76. The Peugeot Got WeirdAn old steel Peugeot frame, a modern one-by drivetrain, and two sets of pedals became my January bike project.
  77. 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.
  78. 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.
  79. Confirmed Turkeys ExistThanksgiving required a turkey, Apply was testing sticker NFTs, and TRX version 10.1.1 kept moving through TestFlight.
  80. 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.
  81. Forget the TimeAt the 2021 Chicago Marathon, I changed my goal and stayed with a teammate who was having a hard day.
  82. 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.
  83. 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.
  84. 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.
  85. No Apps Available to TestThe first weeks at TRX included an App Store approval, an empty TestFlight screen, a first digital operating review, and a new commute to Newport Beach.
  86. LIVE Was Too LiveTRX spent money making live classes that disappeared when the stream ended, so a short product brief grew into the Replay feature.
  87. Newport Pool PartyA Newport Beach apartment turned the new TRX job into a real split-coast routine while Apply and New York kept moving.
  88. Wonky MarathonsPPTC's marathon group came back with three mileage plans, Discord channels, virtual office hours, and no official group runs.
  89. I Won NationalsI finished the sprint duathlon in 1:05:58 and won the men's 35–39 draft-legal national title in Tuscaloosa.
  90. Good Feels All AroundI signed the TRX offer, asked for a May 10 start, then sent a six-part getting-started list three minutes later.
  91. 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.
  92. 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.
  93. 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.
  94. 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.
  95. 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.
  96. 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.
  97. 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.
  98. 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.
  99. We Are OfficialApply launched its 2020 voting-sticker campaign, then the founders stayed close to the support inbox and the first shipping questions.
  100. 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.
  101. A Ridiculous MonthPart of the ceiling came down, the repairs became my job, and our temporary move to Poughkeepsie stopped feeling very temporary.
  102. One Hundred Percent ApplyI passed on the safer job, stopped treating Apply like a side project, and started building the company full time.
  103. Aaptiv, From HomeAaptiv's at-home fitness use jumped, and the company opened a new enterprise and API channel.
  104. The Gutters Fell InThe Poughkeepsie Victorian started leaking during lockdown while I finished references, left Aaptiv, and weighed a CPO offer from Equinox Media.
  105. The Training Sheet Just StopsA 2020 race plan recorded illness, a sore Achilles, and several target races before the schedule stopped during COVID.
  106. Every Rep Leaned LeftA 16-by-400 workout looked fast and consistent, but every repeat showed the same small pacing mistake.
  107. Only One HundredA leadership search wanted someone who had managed 200 to 500 engineers. My org was only about 100, which was suddenly a small number.
  108. Finish Interviews. Learn Stickers.After arranging a possible Aaptiv transition, I planned to finish a few big-tech interviews and learn enough about Apply to decide whether stickers were next.
  109. Two Titles, Both Question MarksA working note reduced a new opportunity to two possible roles and a longer list of questions about people, economics, and the work itself.
  110. Two Broken TreadmillsA messy California International Marathon taper ended with a handmade 2:47:30 pace band and a 2:47:55 finish.
  111. Skip That Bachelor'sCornell encouraged me to apply for its Executive MBA Metro NY program even though I never finished college. I got excited before I got careful.
  112. Tell Me the Truth, LinkedInAfter years of building startup teams, I started asking what a much larger technology company might offer and what I would have to give up.
  113. 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.
  114. 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.
  115. 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.
  116. The Wrong Kind of UnicornThree recruiters pitched senior engineering roles at giant companies. I sent them the same answer: impact, ownership, and an interesting problem.
  117. 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.
  118. 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.
  119. 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.
  120. 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.
  121. 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.
  122. One Hundred Eighty-SevenThe PPTC Marathon Training Group had 187 runners, one volunteer coaching crew, and a lot of TrainingPeaks accounts to load.
  123. Two Forty-Five, PleaseI bought a marathon plan from Brad Hudson, marked it up, then brought the questions straight into Aaptiv.
  124. 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.
  125. 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.
  126. 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.
  127. 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.
  128. 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.
  129. Sixty PercentMy first run after the NYC Half lasted 30 minutes on an Alter-G treadmill at 60 percent body weight.
  130. The Book Was Too BigI finished the RRCA coaching course in Poughkeepsie, then immediately asked if the giant manual came in an iPad version.
  131. 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.
  132. Three Out of FourI ran for the Prospect Park Track Club board with a phone-typed pitch for our great, wild and weird club.
  133. 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.
  134. 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.
  135. 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.
  136. 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.
  137. 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.
  138. 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.
  139. Course Map, IshA Zipcar, a guessed-at Strava route, and a muddy 10K with the Prospect Park Track Club crew.
  140. 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.
  141. 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.
  142. GAP at SixI went looking for three winter running partners at Grand Army Plaza and accidentally found a group.
  143. 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.
  144. 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.
  145. 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.
  146. 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.
  147. 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.
  148. Twenty-Eight Miles, Fifteen PoundsI carried a fifteen-pound pack through a wet 28-mile Catskills weekend with 6,500 feet of climbing.
  149. 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.
  150. 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.
  151. 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.
  152. 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.
  153. 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.
  154. 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.
  155. 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.
  156. 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.
  157. 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.
  158. 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.
  159. Fourth, Then Team USAI finished fourth in my age group at the national draft-legal sprint duathlon and earned a Team USA slot.
  160. One Hundred Twenty EggsI bought 120 eggs and hosted the dyeing crew for Prospect Park Track Club's Easter egg hunt.
  161. Odd Hours in IcelandFour nights, four stops, two South Coast routes, and a work call I was still trying to coordinate from Iceland.
  162. 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.
  163. Run, Eat, Drink, OrganizeThree months after joining PPTC, I moved from morning and weekend group runs onto the club's Social Committee.
  164. 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.
  165. 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.
  166. 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.
  167. Very Close, FinallyThe Poughkeepsie rehabilitation was nearly ready for bank sign-off after an unexpected drainage problem held up the work.
  168. 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.
  169. 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.
  170. Five Twenty-NineI ran 5:29 at the New Balance Fifth Avenue Mile, less than two months after my first 5K back.
  171. The Battery Door BrokeA broken battery door put my Stages power meter out of service until a replacement cover and O-rings arrived.
  172. Take the Cassette ApartI signed up to learn bicycle maintenance, pulled apart a rear wheel, and ended the day debugging a power-meter update.
  173. Twenty Forty-FiveFive months after a stress fracture put running on hold, I raced a Prospect Park 5K in 20:45.
  174. 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.
  175. Open the Door RemotelyA possible leak below my old Portland loft turned into a fast remote response while I was living in New York.
  176. The Network Kept WorkingA recruiter from Reonomy, a product colleague from Peek, and friends from the Shutterstock years all resurfaced while I built the team around Aaptiv.
  177. The New Job Was RecruitingJoining Aaptiv meant building the team, and I needed people who could help me find engineering, technology, operations, and business leaders.
  178. Champagne and Big Buck HunterI gave a short-notice night with friends and colleagues two goals: a giant bottle of champagne and a round of Big Buck Hunter.
  179. 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.
  180. Thirty Calls This WeekI went straight from joining Aaptiv into board prep, thirty recruiting calls, and two nights a week in Python class.
  181. 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.
  182. 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.
  183. 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.
  184. I Needed a Peaceful NightAfter thinking nonstop about an offer from Aaptiv, I declined because I still wanted to build a company from the beginning.
  185. Something More RewardingReonomy had become hard enough that I stopped casually wondering about other jobs and started a real search.
  186. 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.
  187. A Little Out of Left FieldMy work had widened from technology into designers, product owners, and business models, so I asked InVision for a product conversation too.
  188. Two TracksA request for IT leadership candidates became a wider conversation about the work, the team, and whether I might want in.
  189. Still OutsideA Catskills backpacking return and an all-day Habitat for Humanity shift kept the week's plans moving around.
  190. Like Learning a New SportI sent a friend my plainest advice for learning to code: start with a reason, choose Python, save the work, and keep trying.
  191. More Interesting Than ExpectedA short conversation with Vimeo left important questions untouched, but the company itself gave me a reason to keep talking.
  192. Too Much for One CallA conversation about my Shutterstock years made one thing clear: I still wanted the mess and momentum of building early.
  193. I Wanted Better Work ToolsThe software I kept thinking about was simple to describe: tools that helped people and managers do better work together.
  194. Clear the DesksOneButton Studios turned its Brooklyn office into a small Friday-night venue for drinks and a live set by Spider.
  195. Same Flights, Same CampA group of friends booked a week of road riding in South Carolina, giving the spring training calendar a real shape.
  196. Two Days of ScalaA private Scala workshop gave the Reonomy engineers a common place to start, even though they came in with very different experience.
  197. 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.
  198. Nine Months, Crazy ShitA year-old introduction resurfaced after nine months at Reonomy, and the company already felt both brand new and a decade old.
  199. Bourbon and Trailer ParksA Thanksgiving trip to inspect mobile-home parks turned into an introduction for bourbon, space landings, and another strange business conversation.
  200. 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.
  201. CTOs, Tech, Then a DateA portfolio CTO gathering in New York was good enough that I asked the hosts to connect everybody after I left early for a date.
  202. Delete My 1:1sReonomy's product and engineering teams had grown, so I replaced a crowded recurring calendar with open office hours and regular goal reviews.
  203. 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.
  204. CTO, Ironman FinisherA short 2015 bio tried to fit startup leadership, Shutterstock's IPO years, Reonomy, and endurance sport into one paragraph.
  205. Run Club Ran LongA 4.54-mile company run down the West Side turned into snacks, drinks, and a much longer evening than planned.
  206. Indiana With a HammerAnother trip to my childhood home meant plumbing, carpentry, and the slow move from demolition into rebuilding.
  207. Not a Second JobI started sketching a consultancy network that could create a second income stream without becoming another full-time job.
  208. Peer Pressure WinsA teammate's first Photoshop and Illustrator class showed the kind of self-guided learning culture I wanted at Reonomy.
  209. 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.
  210. My Mom Died YesterdayGisi died suddenly, so I headed toward Chicago with no arrangements made and a work calendar that had not moved with the rest of my life.
  211. Bittersweet DinnerAmanda and I planned a last-minute dinner for a promotion that felt worth celebrating and stressful at the same time.
  212. 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.
  213. The Familiar TingleOne bad deadlift repetition turned a familiar warning in my lower back into pain, lost mobility, and an impossible workday.
  214. Dead in the WaterMy phone kept losing data in New York, which meant losing the calendar, Uber, and most of the systems holding the day together.
  215. Pre-Profit InternetMoving Reonomy into a new office meant finding business-grade internet without spending like a business that had profits.
  216. Brass Tax and ValueA smarter-home side project had code, possible partners, and plenty of ambition, but not yet a reason to form a company.
  217. So Fucked for PlacidLake Placid was getting close while work, moving, and training were all fighting for the same hours.
  218. I Quit the MoniesThe shortest explanation I had for leaving a public company to join an early-stage startup.
  219. One CalendarMy first full-time week at Reonomy started with one small, excellent change: three calendars had finally become one.
  220. One Last HandoffMy final week at Shutterstock was about transferring every remaining responsibility before starting at Reonomy.
  221. A Hundred Hours InRoughly 100 hours of early Reonomy work were enough to make me want to give the company my full attention.
  222. Training Fell ApartGetting sick, closing on a condo, and interviewing for a new job pushed training out of my schedule.
  223. Coughing After PhillyA bad chest cold took out the last training days. I still ran 1:26, then went looking for pancakes.
  224. 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.
  225. Do Not Contact My EmployerGoogle invited me to spend a day interviewing in New York. Shutterstock was not supposed to know.
  226. Buy the Fischer GroupI announced a thirty-six-month acquisition plan with no supporting details and one smiling emoji.
  227. Sea to SeaEight days across the Pyrenees changed what I thought a bike trip and my own legs could handle.
  228. Eva Goes to DCThe race trip had one harder logistics problem than the bike: getting Eva there and home without making Sunday worse.
  229. Two Pilsners. One PR.A North Brooklyn Runners team night produced my fastest 10K in twelve years and a questionable pre-race nutrition theory.
  230. Forgot My ShoesWest Point was a two-minute PR with a better swim, a stiff back, tired legs, and bike shoes left in transition.
  231. Let's Dream a LittleThe next twelve months included faster road races, a long swim, another Ironman, and a bike trip across the Pyrenees.
  232. Everybody Was Getting DDoSedA roomful of infrastructure leaders confirmed that large denial-of-service attacks had become an industry problem, not a Shutterstock anomaly.
  233. 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.
  234. Dinner With the Infrastructure PeopleA post-Thanksgiving invitation from General Catalyst was a reminder that the infrastructure community was becoming part of my work too.
  235. Can We Publish This?A request to publish Shutterstock architecture diagrams became a small lesson in supporting engineers who wanted to teach in public.
  236. 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.
  237. Bacon of the MonthNorm's Christmas present arrived as an all-caps email and a promise of recurring bacon.
  238. 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.
  239. Jellyfish and a DecadeThe Cozumel swim had current, jellyfish, and plenty of people who did not finish. I stayed calm and completed the goal.
  240. Wear Flexible ClothingAmanda and I hosted Thanksgiving in Williamsburg with a turkey, pumpkin pies, bikes, board games, and optional head-dresses.
  241. Yes, I Would Like to ParticipateSecond in my age group at Westchester came with a slot for Escape from Alcatraz. The answer was immediate.
  242. Provided the Price SticksShutterstock went public. A friend asked if I was a millionaire. My answer was not quite.
  243. Painless. A Little Clumsy.The first run after a hard race did not hurt. That was enough good news to keep the week moving.
  244. Spend $350 to SwimI found a weekend freestyle clinic in New Paltz and invited a friend with a very honest sales pitch.
  245. I AcceptNorth Brooklyn Runners had no dues, a long code of ethics, and coffee after the Williamsburg Bridge run.
  246. Here's the DealioThe Ironman plan was a beach, a Sunday race, a ferry, and the hardest physical thing I had ever tried.
  247. There's a Startup in ThereOptopus was a little piece of software with enough of an idea inside it to justify lunch.
  248. One Second Broke EverythingA leap second hit the servers while family was visiting, and the phone would not stop being part of the room.
  249. Broke a PedalSeven miles into a triathlon, the pedal broke. The transitions were bad too. I finished anyway.
  250. Joined the GymRetro Fitness followed up about a free day pass. The answer was shorter: I had already joined.
  251. We FiledShutterstock's S-1 became public, and I sent the link to my family with a late Mother's Day call.
  252. I Signed You UpLeadville was high, hard, and apparently something I had decided somebody else should do with me.
  253. Put Some Weight on ItFour guys, two teams, one spreadsheet, and a lifting bet to keep the 5/3/1 cycle honest.
  254. Slept on the FloorThe Williamsburg loft had boxes, a real kitchen, a king bed on the way, and one very happy new tenant.
  255. Williamsburg, PleaseThe apartment search narrowed to a small loft with high ceilings, big windows, and a January move.
  256. Yep, Sounds GoodA Mudder spot opened, the payment could transfer, and my entire decision took three words.
  257. Best Man, Partly Remote?I asked to work part of my brother's wedding week remotely and take the wedding days off.
  258. OutstandingMy performance review came back marked outstanding, with a raise behind it.
  259. Four Pieces, One LoftThe Lower East Side apartment needed a couch, a TV stand, and exactly two dressers.
  260. Put a Pool in the RiverA floating, water-filtering public pool in New York sounded just unreasonable enough to back.
  261. Everything Was My JobMy responsibility list kept growing until the breadth of the role became the problem.
  262. Recruiters Tried to Hire MeAn outside recruiter rewrote our job post and pitched me the role I was trying to fill.
  263. Fun ShizMogileFS, Xen, deployment graphs, and a weekend in the office sounded like a good time.
  264. Seven Months of StartupsIn a fast stretch, I moved from Peek to a hosting company, then joined Shutterstock and kept Ops Dojo going on the side.
  265. Four Days BehindI answered a Volkswagen-van naming thread four days late and suggested Axl.
  266. Goodbye by EmailMy last day at Reality Check passed inside a chaotic weekend, so the proper goodbye came later.
  267. The Withdrawal RequestA death in the family left me behind in two courses, so I asked Baker College to withdraw me from them.
  268. I Officially AcceptedThe second conversation with Shutterstock ended with a Director of Systems Operations job.
  269. Miserable WeekA new Amsterdam data center, school, and a side company all landed in the same seven days.
  270. As If I Didn't Have EnoughThe president of my current company resigned and stayed on the board. My private reaction was immediate and unpolished.
  271. One More ShotSeven months after turning down one Shutterstock job, I asked the company to take another look at me.
  272. Three Weeks, No CardBaker said the school debit card was coming. Classes were getting close, and it still had not arrived.
  273. New BeginningsI asked an old Beatport executive to help build a managed-infrastructure company on the side.
  274. 60K in a FieldTwo nights after watching the Netherlands reach the World Cup final in Amsterdam, I sent one good photo from the trip.
  275. CTO, Written DownReality Check put my CTO responsibilities into a simple roles document, and I immediately used it to help somebody else.
  276. Few Months LateSpring cleaning reached the New York apartment in June, complete with new shelves, a whiteboard wall, and a lot of shoes.
  277. Can Work Count as Credits?I went back to Baker College and asked whether years as an IT director and CTO could help finish the degree I had left open.
  278. One of You Needs to Take ItI made the same Reality Check offer to two former Beatport teammates and tried to get one to bring the other.
  279. We Built an Air CompressorAn old family photo showed my brother and me grinning behind industrial machinery in the machine shop where I once lived.
  280. Sure, Just Call MeI had left Peek for a new CTO job. The old team still needed help with the network, and I still answered.
  281. Passion Now. Safe Later.Facebook, Shutterstock, and Reality Check offered three different futures. I chose the fifteen-person hosting company.
  282. Holy Shit, FacebookA Facebook recruiter found my profile while I was already holding down multiple startup jobs in New York.
  283. Only Young OnceI had a third job offer, a three-person startup that needed to scale, and a very loose theory about burnout.
  284. Sorry for the Email LookupCraigslist replies had failed me before, so I found the founder's address and made sure my half-time Linux application reached a person.
  285. 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.
  286. Baker What?Finishing my degree came down to an expensive New York classroom or a little-known online college built around six-week terms.
  287. The Rad PillowAfter the U-Haul, the filthy apartment, and a couch that barely fit, one homemade pillow made the place look like ours.
  288. Add One SpaceAfter leaving Yodle, I kept helping with its Zenoss monitoring and proposed one space to stop a loose process match.
  289. Official. Again.A few weeks after joining Yodle, I gave notice and took the Director of Technical Operations job at Peek.
  290. Permanently, Last WeekI had finally moved to New York, changed my phone number, and still answered the recruiter calling about another infrastructure job.
  291. 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.
  292. Signed. Then Resign.I returned Yodle's signed offer and NDA, then wrote the letter ending three years at Beatport.
  293. 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.
  294. 1.8 Miles AwayBefore the Yodle interview, I mapped the walk from the East Village apartment to its Flatiron office.
  295. What Kind of Interview?Ten days after applying to Yodle, I got the phone screen and asked exactly what kind of conversation to expect.
  296. Eight Hundred Ninety-Two PercentI applied to Yodle by comparing its rapid growth with the systems I had already scaled at Beatport.
  297. Twenty-Four Months DustyA technical phone screen exposed the difference between doing systems work and reciting it from memory.
  298. 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.
  299. Two Canceled FlightsNew York interviews went well, but two canceled flights kept me there while Denver consulting work waited.
  300. The 1977 CJ5I proposed taking Greyhound to inspect a yellow 1977 Jeep in Grand Junction, and two days later I owned it.
  301. Third Time, Same Unix JobThe Unix administrator job kept appearing on Craigslist, so I sent a third application and explained why I still wanted hands-on work.
  302. Scrub the Network DiagramI offered a security-scrubbed Beatport network diagram as a work sample, but asked before sending it.
  303. My Third JobBeatport, two consulting jobs, and a phone photo sent with one blunt explanation: I wanted a loft.
  304. Twenty Hours, Still GoingA major Beatport deployment had run for twenty hours, and I was still trying to make the meeting for another side job.
  305. February TenthA small Denver studio was approved far enough for a lease, and I accepted a proposed February 10 move-in date.
  306. I Needed a Night ShiftI was Beatport's IT director and applying for night and weekend data-center work because my family needed more money.
  307. The Server Racks WonI studied molecular biology but spent most of my time learning Linux, Unix, storage, and distributed systems on hardware in my basement.
  308. New York, SomehowI was running Beatport's systems in Denver and still tried to turn a New York Unix job into part-time remote work.
  309. A Second Shift From HomeI was Beatport's IT director and answered a Craigslist Linux job with an offer to work remotely at night and on weekends.
  310. Welcome to PhotobucketA Photobucket welcome email confirmed that I had opened an account, but it did not include a first upload.
  311. 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.
  312. Nike+ at the GymA 24 Hour Fitness email passed along a Finish Line offer for the Nike+iPod running kit.
  313. Thirty-Five Dollar FireworksFriends planned a Colorado Rockies game for July 4 with upper-deck seats and the fireworks show included.
  314. Royal Gorge, MaybeA June group email tried to organize a camping and whitewater rafting weekend at Colorado's Royal Gorge.
  315. 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.
  316. apt-get WifeA Digg URL ending in APT_GET_WIFE arrived with one sentence and an antivirus footer.
  317. Zero PEAKS PointsMy ski account ended the 2007–08 Colorado season with no reward points and a $579 Epic Pass offer.
  318. Tee Times Went MobileGolfHub's 2008 mobile launch put Colorado tee-time searches in the same inbox as my Linux servers and Beatport work.
  319. Saturday in BoulderA Thursday group email proposed a Saturday night party in Boulder and asked everyone to pass the invitation along.
  320. Open Source EverythingA friend sent a security link with the subject line, Why All security should be open source.
  321. Linux Admin, AgainA recruiter sent a six-month Linux systems contract while I was already leading infrastructure at Beatport.
  322. Only the Front Is WidebodyI tried to trade the RS4 front end off my Audi S4 and get the car back to stock without shipping body panels across the country.
  323. Do I Need to Reformat?A friend's Linux storage question landed in my Gmail chat while I was running infrastructure for Beatport in Denver.
  324. Hiring Outlook: 2008The new year opened with automated IT job alerts while I was already running infrastructure at Beatport.
  325. Spiced Lamb ShankAn accepted ESPN trade kept our badly named fantasy football league moving in November.
  326. The Apartment Called About the DogA Cherry Creek property manager asked me to call immediately about my dog.
  327. Data Center Specialist, AgainThe same recruiter sent the same data center specialist request on two consecutive days.
  328. The Job Alerts Wouldn't DieDice, Monster, and recruiters kept matching an old online resume while I was already running technology at Beatport.
  329. Refund NeededI paid for an online NFL channel, found it offline, and asked for my money back.
  330. 7:45 Eastern. 5:45 Denver.An ESPN time-zone setting moved our fantasy football draft and started another round of corrections.
  331. Beatport Added BeatportalBy late August, Beatportal was live with news, reviews, podcasts, events, streams, and community submissions around Beatport's music store.
  332. The $29,500 AudiI listed a modified black 2001.5 Audi S4 with a manual transmission for $29,500 on Craigslist.
  333. The Resume Kept WorkingRecruiter messages kept finding an online resume after I used Beatport's infrastructure numbers in job applications.
  334. Playing Catch-upFour Facebook photo-tag notices arrived from an album called Playing Catch-up.
  335. Print Four and FiveA friend sent one instruction before the Nuggets played the Lakers: print tickets four and five.
  336. Two Welcome EmailsTwo 24 Hour Fitness welcome messages marked the start of a new gym membership.
  337. The Dog Was StayingAfter weeks of considering a new home for my Weimaraner, I decided to keep working through the difficulty.
  338. Director at Twenty-TwoMy Beatport title changed from Network Administrator to Director of Information Technology when I was twenty-two.
  339. One Click from LiveA classified post about finding a new home for my young Weimaraner was drafted but still waiting for confirmation.
  340. Network AdministratorA Thanksgiving email preserved my first Beatport title and the ordinary mail system surrounding a global store.
  341. Beatport OfferA September interview at a small Denver online music store turned into a written systems-administration offer six days later.
  342. Real Estate, Then ServersOne September day mixed an OptiTrex real-estate side project with a request to discuss another systems job.
  343. Linux on His PhoneA friend sent me a link to a Linux port for his Windows Pocket PC phone.
  344. Dogs Allowed or No DealSearching for an August weekend in Estes Park came down to one requirement: the puppy had to be allowed.
  345. Answer by MondayA Friday company visit turned into a written systems-job offer with a Monday deadline.
  346. Five Hours Was OptimisticI finished the 2006 Leadville Trail Marathon in 5:37:50, 74th out of 238 finishers.
  347. Ride to Work. Run Leadville?I was biking to work, training for a difficult marathon, and considering the Leadville Trail 100 run.
  348. The Resume, TwiceI applied through Dice, then sent the network-administrator resume directly because I did not trust the automated system to deliver it.
  349. I Bought My NameA June 2006 registrar notice confirms that I had registered chrisfischer.info and changed the domain to locked status.
  350. Someone Forgot the DomainA BMX forum disappeared behind an advertising page when its domain expired, then returned after the operator renewed it.
  351. Chicago for a WeddingThe itinerary and my photos line up: I flew from Denver to Chicago for a wedding weekend in May 2006.
  352. Denver Was HiringA Dice employment report arrived while I was applying for network, Linux, Unix, and systems roles around Denver.
  353. 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.
  354. $8 Million LaterWestar Aerospace acquired SimAuthor for $8 million while I was responsible for its network, systems, security, and in-house data center.
  355. Linux Jobs. All of Them.One Monday produced a pile of resumes for Linux support, network administration, and consulting work.
  356. The S4 InterrogationBefore buying a used 2001 Audi S4, I sent the owner a detailed list about modifications, maintenance, mileage, and how it had been driven.
  357. Back to CU?While working at SimAuthor, I sent my resume to former CU colleagues and asked them to keep me in mind for administrator roles.