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Best of Bootstrapping: Bootstrapping to Y Combinator and $10 Million Series A

Posted on Saturday, Nov 30th 2019

UpKeep Maintenance Management CEO Ryan Chan took a hobby project that he bootstrapped with a paycheck and managed to get into Y Combinator. From there, he raised a $10 million Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution thus far.

Sramana Mitra: Let’s start from the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Ryan Chan: I was born in Kentucky. My family moved there for my father’s job. But then, we quickly relocated to California. I grew up and was raised in a small suburb in Los Angeles called Oak Park. Not many people know where that is, but it’s about 20 miles west of downtown Los Angeles.

I’ve always been fascinated with building things and I think that’s one of the reasons why I got into entrepreneurship. I went from elementary school to middle school, to high school in that small suburb. I went to college at Berkeley up in the Bay Area.

I pursued a chemical engineering degree and my first job out of college was working in a manufacturing plant, driven by my fascination for building things. That was where the first inspiration for Upkeep came.

Sramana Mitra: What did you do when you came out of college? What year was that? What time frame are we talking here?

Ryan Chan: I graduated college in 2013. My very first job was working in a manufacturing plant that was spun out of DuPont Chemicals. We manufactured membranes for reverse osmosis for a little bit of brackish water. So, these big cylinders can be pushed in dirty water and they suck out very clean water that you can use for even things like drinking.

Sramana Mitra: Interesting. So I actually know quite a bit about reverse osmosis because we invested in a company out of the East Bay in San Leandro called Energy Recovery Incorporated. I don’t know if you’ve ever heard of this company. 

Ryan Chan: I actually haven’t. But yes, we were manufacturing reverse osmosis membranes. 

Sramana Mitra: Where was this based out of? 

Ryan Chan: My first job was in Santa Barbara. So I took the leap from Berkeley to Santa Barbara. My title there was Process Engineer. A Process Engineer thinks about how to improve manufacturing lines. How do we make it go faster? How do we reduce downtime? How do we speed up efficiencies and productivity of our entire team?

That’s where I got my first start into building things and also thinking about how we can improve the lives and processes of our company.

Sramana Mitra: What happens after that? Bridge us into the story of founding Upkeep.

Ryan Chan: It might help to give a little bit of context into what UpKeep is. We build software for maintenance teams. The most common use case that I always give is imagine you’re in a manufacturing plant and a piece of equipment breaks down.

You basically use UpKeep to snap a picture, create a work order, and shoot it over to the facility manager who can prioritize and send out a technician to go fix it. It’s this group collaboration task management tool geared towards facility and maintenance managers.

So you can probably see where this ties into my very first job. I was thinking about improving our process and improving efficiency around the plant.

One of the big things for us was thinking about how we can reduce downtime for our equipment. If we’re able to reduce our downtime for equipment, that basically meant that we could produce more goods and generate more revenue for the company. So what we said was, “We’re going to purchase a very expensive piece of software that will help us manage all of our preventative maintenance and streamline our operations.” We did that.

We paid a lot of money. Everything was desktop-based. If you imagine a manufacturing facility, no one is sitting at a desktop. What happened is our techs are out in the field with that same exact use case. They get a work order. They’d write all the notes down on a piece of paper and pencil.

Now that we have this new software, they had to come back to the office at the very end of their day and retype all of their notes back in. Instead of making their days, lives, and jobs easier, this software actually made it way more cumbersome.

So I said, “I want to find something that’s extremely easy for technicians out in the field to use.” That’s where they are spending 90% of their day. I want to do it with this mobile-first approach so that, again, it makes their day, lives, and jobs easier. While I was working as a process engineer, I couldn’t find anything that was mobile-first that our company could really use.

So I taught myself how to code. Out in Santa Barbara, I took a community college class on weeknights and weekends. This iOS programming class is the very first programming class that I had ever taken. It was from 6 PM to 10PM, three times a week. That was my very first introduction to programming.

I said, “I want to use Upkeep as my first project.” I never thought it was going to be a big thing. I never thought I would turn this side project into a full time career; let alone a company that it is today. I just started building.

Our conversation continues here.

This segment is a part in the series : Best of Bootstrapping


. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK
. Ownership Matters
. Vainu Co-founder Mikko Honkanen Bootstraps from Finland
. Entrepreneur Couple Bootstraps to $10M from Colorado
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million
. Freightwise Bootstraps to $33 Million
. Bootstraps First to $5M ARR, Raises $10M Later
. Bootstraps in Europe, Raises Money and Goes Global in the US
. English Major Bootstraps a Tech Company
. Bootstraps with a Paycheck to $15M from Tennessee
. Queue-It Bootstraps from Denmark to the US
. Bootstrapping A Virtual Company To $25M
. ActiveCampaign CEO Bootstraps Using Services to $40M
. Alteryx Bootstrapped with Services to a Public Unicorn
. Inspyrus Bootstraps Using Services to an Awesome Business Model
. CEO Bootstraps Using Services to Millions from Russia
. Wiredrive CEO Bootstraps Using Services to $10M
. Scaling to Over $10M by Bootstrapping Using Services
. Bootstraps Using Services from Poland to a US SaaS Company
. ButcherBox CEO Bootstraps a Perishable Meat Business to Significant Scale
. Waveform CEO Bootstraps to $8M
. Bootstrapped Entrepreneurship from Estonia
. From Laid-off Engineer to Successful Startup CEO
. Imagine Easy Solutions CEO Bootstraps to Exit
. BannerBuzz CEO Bootstraps to $35M
. Bootstrapping a Virtual Company to Scale
. Bootstrapping Using Services from Wisconsin
. Best Tactic for B2B Startups
. Bootstrapping by Piggybacking from Romania
. Bootstrap First, Then Scale with VC Funds
. Bootstrap to +$10M First, Raise Money Later
. Madwire CEO Bootstrapped First, Raised Money Later to $120M
. Bootstrap Using Services First, Raise Money Later
. Wonderful Bootstrap with a Paycheck Story
. RushOrderTees CEO Bootstraps to $23M
. Bootstrapping with Freemium and Free Trials to $13M
. Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+
. Bootstrapping with Affiliate Marketing
. Bootstrap to Exit, Bootstrap Again, Then Raise VC Money

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