6 Degrees of YC Separation

Growing up, moving to San Francisco, working in startups, and becoming a YC Founder.

Kyle Mack
Kyle Mack
Dec 31, 2018 · 6 min read
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My Co-founder and I have been accepted into the Winter 2019 Y Combinator batch.

I’ve always wanted to start my own business. My dad and grandfather were both small business owners. Growing up, I mowed lawns, painted houses, and flipped beat-up cars from the Vermont auto auction to make a few extra bucks.

During my first year of University, my friend and I delivered liquor to the dorms for $5 per bottle — a bargain during Montreal winters.

That summer, I met Patrick, who was interning at a Montreal startup.

Vermont offered no exposure to technology companies or startups, but that summer I watched Patrick hack together apps in a weekend that could be used by thousands of people the next day. I was hooked.

(more about how Patrick changed my life later)

I applied for the Winter 2013 batch of YC as a solo, non-technical founder, with no product.

Soapbox was going to be the next Facebook…😑

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Soapbox application for YC W13
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Really nice Soapbox mockups (December 2012)

I wasn’t going to be a founder anytime soon.

My first job out of University was at AnyPerk (YC W12). After applying to a “Who’s Hiring” post on Hacker News, I was hired as a BD Intern. AnyPerk (now Fond) had 6 employees at the time. I worked remote for the first month and moved to San Francisco shortly after.

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Moving Day, July 2013 — first time in San Francisco

I learned the basic mechanics of sales over the next year and a half and got promoted to an Enterprise Account Executive and Team Lead role.

A few takeaways thinking back on that time:

  • Solve problems where the solution is a “Must-have”, not a “Nice-to-have”.
  • Things will always be broken.
  • Strong company culture is extremely important.

One day, I got a call from Patrick. He had been accepted into YC and was moving to San Francisco to work on his new business, Hive (YC S14). Needing a place to stay, Patrick and Ian, “The Canadians”, slept on my couch and incorporated their business out of my apartment in The Mission (shoutout Casa Dolores).

A couple of weeks before the end of YC, I asked Patrick which companies in their batch seemed promising.

“ I know a couple of crazy French guys that are building a background check company that seems cool.”

I met Daniel and Jonathan the following week and shortly after, accepted a role as the first sales hire and 5th employee at Checkr.

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Some really great French and Canadian friends

During my 4 years at Checkr, we built a profitable business that has raised $150M in funding and employs 300 people. It was an incredible experience.

I was fortunate to lead Strategic Sales and Solution Consulting, where I was responsible for the sale, solution design, and implementation of Lyft, Zillow, Postmates, GrubHub, Thumbtack, and many others.

I led our go-to-market plan as we transitioned to selling into the enterprise, saw how product roadmaps were built, customer success teams were designed, and operations and support teams were scaled.

There are so many learnings that I’m excited to share, but for now, I want to highlight a few thoughts that I believe are helpful for high growth, early-stage companies.

(I pulled these from a doc I started, “Notes to myself”. I highly recommend starting a similar document for keeping track of thoughts/learnings over the years.)

Interview for the ability to execute: Startups are an exercise in execution. Regardless of how many hours have been spent researching and planning, if you are unable to execute, a business cannot succeed and the ability to execute is largely dependent on the team. Hiring people that have a track record of taking projects from inception to delivery and who actively seek out projects to own is critical. It can be extremely easy to become blinded to a candidates lack of experience owning projects because they have a flashy resume.

Set up a framework for accountability: When a company is small, it is easy to understand who is doing what. As companies grow, this changes. It’s important to set up a framework that allows individuals to hold themselves accountable to the other members of their team. At Checkr, the cadence of meetings I found to be both simple and effective was:

  • Team Kickoff (Weekly, Monday morning) — Each team member presents 1–2 sentences on their commitments for the week. Track these in a shared doc.
  • Project Deep Dive (Weekly, midweek) — A 1:1 hour between each individual contributor and their manager to deep dive on weekly commits and other projects.
  • Team Debrief (Weekly, Friday afternoon) — Each team member presents on their performance against their commits for that week.

By following this simple cadence, team members hold themselves accountable to one another, projects make progress, and everyone is better aligned.

Document the right amount of things: In a fast-moving company, building documentation and process can feel like a distraction and waste of time. There will come a day when you will want to double the size of a team in a short period and without the right documentation in place, it will be extremely challenging for new team members to be effective in their role. There is a different bar of process and documentation needed for each stage of a company. The important thing is to continue to evaluate progress and align it with the growth targets of the business.

Outside of the lessons that I’ve learned, I was also lucky enough to continue to increase my exposure to YC while at Checkr. I used to think the only way to be “part of YC” was by becoming a founder. My time at Checkr has shown me that this is not true. I’ve been able to meet many of the members of the YC team, have led sales office hours sessions for a previous YC batch, and have helped multiple YC teams set up their sales and go-to-market strategies.

I am extremely grateful to everyone who has supported me. I could not feel more fortunate.

We wrote our application on October 1st and got our acceptance call on November 2nd.

After what now feels like years of training, here we are.

My Co-founder, Kurt and I have been accepted into the Winter 2019 Y Combinator batch.

Our company, Middesk will be launching soon and we can’t wait to tell you all about it.

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