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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122 stories / Teams. Newest first.

  1. Apply Took DUMBOThe Apply team was together in DUMBO while several people were visiting New York.
  2. Every Dollar MattersLoop needed a raw Alpha in ten days, so I hired engineering help, handed out repository access, and joined a very small team sprinting through the product gaps.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.
  10. Woah, Shit's BrokeTesting the TRX class flow produced an error screen and two very direct product alerts in under two minutes.
  11. 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.
  12. One Hundred Percent ApplyI passed on the safer job, stopped treating Apply like a side project, and started building the company full time.
  13. 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.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. 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.
  19. 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.
  20. Three Out of FourI ran for the Prospect Park Track Club board with a phone-typed pitch for our great, wild and weird club.
  21. 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.
  22. No Code, Still InCyral asked me to advise on database security. I wanted the work, but first I sent Aaptiv a plain conflict check.
  23. 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.
  24. 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.
  25. 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.
  26. 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.
  27. Seventeen CSVs LaterI turned Aaptiv activity data into seventeen queries covering the path from the home screen to a completed class.
  28. 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.
  29. 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.
  30. Thirty Calls This WeekI went straight from joining Aaptiv into board prep, thirty recruiting calls, and two nights a week in Python class.
  31. 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.
  32. I Hired No ManagersAt Reonomy, I hired individual contributors with room to grow and promoted managers from the product and engineering team.
  33. Something More RewardingReonomy had become hard enough that I stopped casually wondering about other jobs and started a real search.
  34. 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.
  35. 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.
  36. Two TracksA request for IT leadership candidates became a wider conversation about the work, the team, and whether I might want in.
  37. Continuously Shipping ValueA newly created engineering-director role recognized the kind of cross-team leadership Reonomy needed next.
  38. 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.
  39. Hyper MinimalMy favorite one-on-one format used five repeated questions, fifteen minutes of discussion, and very little ceremony.
  40. Forty-Eight WeeksReonomy was looking beyond the usual recruiting channels, and a nearby startup pointed me to a full-year engineering internship program from NUS.
  41. More Interesting Than ExpectedA short conversation with Vimeo left important questions untouched, but the company itself gave me a reason to keep talking.
  42. A Lot of HorsepowerMy answer about Reonomy was short: I loved the team, the work was expanding, and the next few months would tell us a lot.
  43. Almost Ready to ShowThe side project had moved from an idea I kept describing to something I hoped a trusted friend could try within weeks.
  44. Too Much for One CallA conversation about my Shutterstock years made one thing clear: I still wanted the mess and momentum of building early.
  45. I Wanted Better Work ToolsThe software I kept thinking about was simple to describe: tools that helped people and managers do better work together.
  46. I Need a ManagerI had let the management system slip while Reonomy grew, and the number of direct relationships was no longer workable.
  47. 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.
  48. The Offer LandedA December engineering offer moved through questions, missed calls, and benefit details before the candidate chose to join Reonomy.
  49. 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.
  50. The Hole Before the RoadNine months after I joined Reonomy, a long onboarding email showed why new engineers needed the product history as much as the preferred architecture.
  51. The Director Search Woke UpAfter pausing the role in September, I spent early December turning engineering-leadership referrals into calls, breakfasts, and real conversations.
  52. Medium Data, Not Big DataDinner with startup friends turned into a late-night note about hiring, users, APIs, and why their business did not need a giant data stack yet.
  53. A Few Days LateA former employee asked to exercise vested options just after the window lapsed, and I argued that being legally clear did not settle the fairness question.
  54. Scala Goes to LAReonomy was finishing a rebuilt data-processing pipeline for Los Angeles while I looked for temporary help to expand the ingestion team.
  55. Tell Me AnonymouslyBefore Reonomy finalized its company values, I asked the team to say what mattered through an anonymous form or a direct conversation.
  56. 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.
  57. CTO, Ironman FinisherA short 2015 bio tried to fit startup leadership, Shutterstock's IPO years, Reonomy, and endurance sport into one paragraph.
  58. Run Club Ran LongA 4.54-mile company run down the West Side turned into snacks, drinks, and a much longer evening than planned.
  59. 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.
  60. Hold the DirectorI paused an engineering-director search and decided Reonomy needed several team leads first.
  61. Peer Pressure WinsA teammate's first Photoshop and Illustrator class showed the kind of self-guided learning culture I wanted at Reonomy.
  62. Party by FiveAn all-day Reonomy hackathon mixed prototypes, Xbox games, drinks, and two ideas that looked worth taking toward production.
  63. Button This UpReonomy's new office needed internet, phones, weekend access, and one final push before the team could work there Monday.
  64. It Went Out EarlyA feature reached production before it was supposed to, and the repair started with an apology to the teams who depended on the release process.
  65. VP Engineering, Pulling CableI came back from family matters to an office move and an urgent search for somebody who could pull Cat5 cable.
  66. A Pubic Hair AwayWe needed a narrower product, a reliable data API, and mock routes that let the front-end and data teams work in parallel.
  67. Pick a WikiReonomy needed one searchable place for its processes, and I did not want the tool choice to become another long project.
  68. Stop Everything MondayRecurring outages had become serious enough that I ordered a full work stoppage until two critical blockers were resolved.
  69. Wildly UngroomedThe backlogs were a mess, so we put the work on a wall and started building a cadence around it.
  70. One Last HandoffMy final week at Shutterstock was about transferring every remaining responsibility before starting at Reonomy.
  71. The Deck Before the JobBefore I joined Reonomy, I made a deck covering cross-functional product teams, engineering leadership, hiring, and onboarding.
  72. Christmas Week Security CallDuring a possible Shutterstock account-security incident, I tried to get the technical investigation and customer communication moving at the same time.
  73. Do Not Contact My EmployerGoogle invited me to spend a day interviewing in New York. Shutterstock was not supposed to know.
  74. Storage Was Everybody's ProblemThe storage problem was too important to keep inside one operations circle, so I started identifying product owners and engineers to involve early.
  75. Managers Need Training TooAs the organization added more leaders, a shared management workshop offered a way to build continuity instead of leaving everyone to improvise.
  76. Break It on PurposeA failed firewall had left the production pair out of sync, so the safer choice was a controlled maintenance window instead of waiting for another failure.
  77. Everyone Ships CodeAt the 2013 OpenStack Summit, I explained how Shutterstock provisioned virtual machines and physical servers through one automated system.
  78. Can We Publish This?A request to publish Shutterstock architecture diagrams became a small lesson in supporting engineers who wanted to teach in public.
  79. Same Tools, Different SizeDev, QA, and production did not need identical scale, but they did need the same tools, deployment path, operating system, and testing discipline.
  80. Hack to the FutureOur Shutterstock hackathon project did not win, but the demo landed and the idea was good enough to keep building.
  81. We Needed More HumansA June recruiting email described Shutterstock's WebOps team as it looked for operations engineers for the company's next phase of growth.
  82. Search Had One GuyA departing specialist created a knowledge gap around Shutterstock's search infrastructure and started a discussion about coverage and hiring.
  83. Ten Minutes. Go.The first opportunity assessments for Shutterstock's technology syndicate were ready for a ten-minute leadership review.
  84. Who Owns This?A March thread asked whether Shutterstock had formal technical owners and started a written process for defining the role.
  85. Offsite: Uptime FirstThe agenda for a March technology leadership offsite started with service uptime, programming languages, syndicates, and more consistent environments.
  86. Humans Worked. Alert Failed.The Shutterstock mobile site worked when we tested it by hand, but one automated check still failed and needed an owner.
  87. Define DevOpsA friend needed a DevOps hire. Before naming anybody, I needed to know what he meant.
  88. One Second Broke EverythingA leap second hit the servers while family was visiting, and the phone would not stop being part of the room.
  89. Bring Him InA technical recruiting conversation moved from an introduction to a phone call to one short decision.
  90. Still HereThe whole operations team was still provisioning a new data center, so the next database cutover could wait.
  91. Moderately CrazyShutterstock had grown. The office network had grown with it, just without much of a plan.
  92. Make Local WorkThe infrastructure goal was basic: every developer should have a standard environment that worked on a laptop.
  93. Before Monday Showed UpWe put real load through a new Shutterstock network layout over the weekend and found a bottleneck before Monday traffic arrived.
  94. Tech Happy HourEvery other week, the technical team stopped working long enough to eat and drink together.
  95. One Petabyte. Three Sites.An October announcement draft documented more than one petabyte of Shutterstock storage across three sites.
  96. How Long on Diesel?Hurricane Irene produced one blunt question about backup power and time.
  97. Contributors Couldn't UploadAn upload-server issue blocked part of the contributor base while the team restored storage and explored a reroute.
  98. Four Rooms, One HangoutDevelopers and WebOps troubleshot one issue from two Manhattan floors, Denver, and my apartment.
  99. OutstandingMy performance review came back marked outstanding, with a raise behind it.
  100. Three to Six-ThirtyThe site stayed up through an overnight database and search problem whose cause was still unclear.
  101. Everything Was My JobMy responsibility list kept growing until the breadth of the role became the problem.
  102. Tier I, PleaseThe 2011 email said “Tier1,” but the real idea was to use the facility as a foundation for infrastructure we designed ourselves.
  103. Eight to Ten SecondsThe maintenance plan accepted one small site blip to reduce a much larger power risk.
  104. Data Server IssuesIssues around the data servers had contributed to a recent outage, so I asked for a conversation that day.
  105. Replication LagReplication lag had shown up again, and I wanted systems and development looking at it together.
  106. Recruiters Tried to Hire MeAn outside recruiter rewrote our job post and pitched me the role I was trying to fill.
  107. Kill Spanning TreeThree of us went to the data center to replace the old switches and simplify the network.
  108. The Firewall Didn'tA failover failed, the console path worked, and my laptop was sitting at happy hour.
  109. Fun ShizMogileFS, Xen, deployment graphs, and a weekend in the office sounded like a good time.
  110. Call Me When It Goes DownTwo months into Shutterstock, I asked the systems team to call me for every critical alert while I learned the environment.
  111. Goodbye by EmailMy last day at Reality Check passed inside a chaotic weekend, so the proper goodbye came later.
  112. I Officially AcceptedThe second conversation with Shutterstock ended with a Director of Systems Operations job.
  113. 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.
  114. One More ShotSeven months after turning down one Shutterstock job, I asked the company to take another look at me.
  115. CTO, Written DownReality Check put my CTO responsibilities into a simple roles document, and I immediately used it to help somebody else.
  116. 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.
  117. 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.
  118. Please Take This JobReality Check needed an infrastructure engineer. I wanted somebody I trusted and was already tired of interviewing.
  119. Two Days, Cool GraphsReality Check tried two-week sprints, small tasks, daily updates, and a chart that became interesting almost immediately.
  120. Passion Now. Safe Later.Facebook, Shutterstock, and Reality Check offered three different futures. I chose the fifteen-person hosting company.
  121. New Title. Same Tests.My Beatport signature now said Director of Information Technology, but I was still sending messages through the system by hand.
  122. Director at Twenty-TwoMy Beatport title changed from Network Administrator to Director of Information Technology when I was twenty-two.