3 years, 2 rejections: Journey to YC S20
After 3 years, 3 interviews, and 2 rejections, I got accepted into YC. Here’s how that happened.
I shared my journey to Y Combinator as a homage to all the unknown blog/twitter handles that helped me with advice, application review, and mock interviews. It felt only right to pay it forward. My dms are open for application help or mock interviews.
2019
April: Finally get to launch Vitable months after ideation (More on these trying months some other time)
Launched Vitable in Philadelphia as uber for urgent care - call, pay $79, and have a nurse practitioner in your home in 2 hours.
Driving 3 hrs one-way back/forth from Philadelphia to State College 4 times a week for classes.
Had early teammate quit because of health issues
Recruited someone to apply to YC S19 with since (I thought) YC did not like solo founders
We get an interview, they quit a few days before flying to SF
‘Don’t you have a co-founder?’ - knew I’d gotten rejected immediately, spent next 9 min getting advice
Aaron Epstein sent me a really thoughtful email that strengthened my resolve to continue
May: Postpone Microsoft internship to fall. Bunker down and work
Beg my recruiter to move internship to the fall (nearly impossible). Only Waterloo kids get that privilege. But it works.
Go back to work. Switch to subscriptions instead of fee for service
Get a kiosk at the local mall and start selling healthcare coverage for 1.5 months
Few of the shoppers sign up. But the mall employees enroll.
Host pop-up wellness clinics w/ our nurse practitioners at WeWorks in Philly
Few tenants sign up. But the janitors & supporting staff enroll
2 months later, churn is high - credit cards expire, lost jobs, or no money. They still wanted the service.
Our (beautiful) Mall Kiosk for $600/month
August: Detour to Microsoft Internship for 3 months w/ contract sales rep on the ground in philly
Moved to Seattle to finish my last internship at Microsoft
Lost motivation, couch surfing for the first month: thanks to Quentin, Arsala & Farabi
Move to Airbnb next to golf course in Bellevue. I spent a lot of time trying to learn to swing a club instead of building.
Indifferent about the service I’m building on Xbox. Team is awesome. Work is stimulating. But mind is elsewhere.
Roommate has heart attack and dies. Other roommate has major PTSD and is hateful of most people (So many stories here). But he gives me golf clubs and teaches me how to swing a golf club
Finish internship. Accept full-time offer for April 2021 - 1.5 yrs out (unusual). I have 1.5 yrs to make Vitable work.
No real sales growth for prior three months. Demotivating.
December: Return to Kenya for the first time in 10 years to reflect.
First time since immigrating to Philadelphia 10 years prior.
In a decade, I’d gone from living in a cramped basement with six members of my family, in one of the worst neighborhoods in Pennsylvania, to Microsoft.
Returned after the new year feeling excited about the next 10 yrs. Hoping to replicate the previous decade’s delta
2020
January: Take a sabbatical from school to focus on Vitable full time
Have to jump through major hoops to re-enroll to school after fall internship. Decide to focus in and find a way to make Vitable work.
Remember that high churn from those hourly mall and WeWork workers…
We pivot to sell to those same hourly workers through their employers.
Payment via payroll deduction, no credit cards, reduced churn, sales vs marketing
Target demographic: employers of $10 - $15/hr employees
Door-door sales. Showing up at random office buildings. Getting chased out of many, some very receptive.
$1k MRR in January. Figuring out B2B process
Dan the man joins me part-time while moonlighting at JPM
February: Things start to turn around. Building pipeline
Focused in on daycares and home cares. Pipeline is full, not many closes yet
Revenue is now close to $2k MRR. Ramen profitable
March: COVID hit. Sales rep quits.
Contract sales rep quits in late March. Not great. Have to reconfigure prospecting, lead gen
COVID hits. Employers have unexpected urgency to offer affordable health coverage to their employees
Quickly added ability to do in-home COVID tests for our members
Huge need. Supercharged growth
Conor joins as Biz dev intern -> sales rep. Helps keep momentum high.
Doubled in March, April, +80% May
Applied to YC again…this time as a solo founder, weeks late. No recommendations.
Got an interview. Considered not going through the prep process and just ‘bootstrap.’ Lolz I have Farabi to thank for talking me out of that stupidity
April: (Obsessive) YC interview prep and virtual interview
Did a bunch of interview prep with YC alumni that posted on twitter.
All interviews were virtual, which I preferred.
I’d had an interview for the summer batch each of the previous 2 years. Always on my birthday on April 25th (yes, YC has ruined my last two birthdays).
This time was different…on the 26th.
The interview was with Michael Seibel and 3 others. I remember very little about how it actually went.
10 minutes speed by. I get an email for another re-interview on the next day. At least they didn’t turn me down right away. Go for long walk.
Re-interview: At least I’m not dead yet
Have one more prep interview w/ generous soul before re-interview. Big difference-maker.
This time the interview is with Aaron Epstein, Tim Brady & Kevin Lin. It seems to go much better. I was more aware & composed.
I go on a looongg walk for 4 hours just replaying the interviews over and over in my head.
I get a call as I’m getting back to my parents’ from an unknown number.
It’s Aaron. I got in. After 3 years, 3 interviews, and 2 rejections, the 3rd time really is the charm. I finally get in.
What was different this time compared to the other times over the three years?
I had real traction, growth, compelling story arc…and pints of luck.
May - August: Y Combinator S20, First Virtual Batch
Lived up to the hype, especially since I had no network in SV
Focused in on affordable primary and urgent care coverage for living wage employees instead of urgent care membership.
Raise seed (pre-seed?) from awesome firms and angels.
Dan the man joins full-time after the batch; I stop paying Conor through Venmo and we officially set up Gusto.
The team is now Conor + Dan + I.
September - TBD: We’re hiring (is 10x still a thing?) engineers, sales reps, writers…etc
If you’re passionate about rethinking how healthcare fundamentally works for the majority of Americans, I’d love to chat. Kitonga [at] vitablehealth [dot] com
Here are some of my takeaways from this past year’s journey. Painful lessons I don’t want to forget.
Vitable - We’re building a health plan from the ground up - starting with primary and urgent care coverage.
Special thanks to my family: Mom, dad, Job, Mercy, Grace, Dante, Lesly & Lesley. Vitable would not exist without their selfless help.
And friends: Adam, (Xiang) Codez, Dan, Farabi, Conor & J.O. At one time or another, they’ve influenced what Vitable is today.
And Microsoft: Without whom, I would not have had the cash to drop out.
This' so inspiring Joseph. You've got what it takes to achieve big thing. Best wishes from India. #keepImproving
Incredible journey! We are so proud of you and always here to support you 100% .