Startups

How I Created A $350 Million Software Company Knowing Nothing About Software

Comment

Image Credits: a40757 (opens in a new window) / Shutterstock (opens in a new window)

John Sung Kim

Contributor

John Sung Kim is the founder of Five9 and DoctorBase (acquired by Kareo).

More posts from John Sung Kim

I’ve always wanted to make a lot of money, have people pay a lot of attention to me and do a lot of exciting things. I just never knew how.

Many of my friends who are founders of their own companies tell me how they exhibited the entrepreneurial spirit as a kid — they sold candy out of their backpacks, had a landscaping business during the summer, etc. They created value and learned the virtues of hard work early on.

But that wasn’t me. I created a horse-racing simulation game in Applesoft BASIC in Manhattan Beach Middle School’s computer classroom and ran a small gambling operation. I mean, who could blame me? The teachers left that class completely unattended during recess and lunch, as if they couldn’t fathom how any kid could get into trouble playing with those large calculating typewriters.

However, making a few dollars to buy an endless stream of Atari games and learning how to collect from the bigger 8th graders didn’t teach me anything about building a tech company. By the time I decided to move to San Francisco, I was completely and totally clueless.

Just as bad was my sense of timing. By the time I entered the job market the dot-com bubble had burst, leaving scores of smart people unemployed and a wave of VC firms bust. A lot of people were leaving the Bay Area to go back to wherever they had come from, but I was too stupid to know anything about the logical decisions people made.

The discount brokerage firm where I clerked gave us all two weeks of training in how to execute online stock trades at one of their call centers in San Diego. That’s when I had my brilliant idea (except it didn’t turn out to be brilliant until I changed it a few times).

The call center manager who monitored our training was in his late twenties and had a smug grin on his face all day, every day. “This call center system I’m teaching you costs $30,000 a person,” he mentioned, several times. He smirked a lot and I despised him.

It struck me that if I could build cheaper call center software, I could make my own software company — and have revenge on The Smirker.

The stars must have been aligning for me because shortly thereafter, my college roommate, who I nicknamed “The Fro” (I give nicknames to everyone for whom I have a deep affection), called to tell me (brag) that the call center software startup he worked for had been acquired by Cisco.

He hadn’t made much as a late-stage employee, he admitted, but he had a taste for what could be, and encouraged me to fly to Boston to discuss creating our own startup. “After all,” he said, “you’re good at selling shit.”

I wasn’t sure that was a compliment, but I bought the plane ticket.

After a weekend of discussing dreams and man-feelings, we got each other excited enough to decide to quit our jobs the following Monday. I gave my two weeks notice.

Then something odd happened. The Fro wouldn’t answer my calls all day that Monday. On Wednesday he finally called me and said sheepishly, “Brooo. You know what Bro? I decided that it’s not a good idea for me to quit my job right now. Seriously. I’m so sorry.”

I had $5,000 in my bank account, and I seriously thought of spending $1,000 of it just to fly back to Boston to punch him in the face. Instead, I hung up the phone and punched the wall. Maybe a few times.

Then I called him back and asked him, as calmly as I could, if he knew of anyone else at his newly acquired startup that might want to create a software company with me. I reminded him that I was good at selling shit. He introduced me to “Tooter,” who, it turned out, was heading my way to go snowboarding in Tahoe.

When we met at Heavenly Ski Resort I discovered an obviously brilliant guy who disliked corporate life and had an unbridled affection for activities that may not have been fully legal in the state of California. But hey, we all had issues.

He explained to me that he and The Fro had worked at a startup that created software for call centers, an ages-old industry they had revolutionized by adding a .com to the name of the company.

Because I was an entrepreneur (unemployed) now, I told him that we should just recreate that class of software, and he agreed. To his credit, and somewhat to my amazement, he sent an email to his boss and quit that night. A few weeks later he sold his house in Boston and bought a new one in the Bay Area.

But what made him such a risk taker and brilliant programmer also made him a supreme asshole at times. Knowing nothing about software companies, many of my questions were met with a question of his own, his favorite being, “Are you a fucking idiot?”

There were so many depressing nights alone that often I would watch my favorite movie, The Shawshank Redemption, over and over, mindlessly. Maybe seeing Andy Dufresne enduring so much shit made me feel better about my own situation.

Clearly, I needed help (therapy), so I asked my former boss at the discount brokerage firm if he knew of any angel investors.

Thankfully, he introduced me to his favorite day-trader client and explained to him that I was a promising entrepreneur and that Tooter was an amazing engineer, which he absolutely was. I explained to the investor as passionately as I could that I was going to build a successful software company or die trying, and that I was into self-preservation, so…

The day trader pointed to a picture of a small jet on his office wall and said, “I want you to help me buy this.” He then wrote us a check for $150,000 on the spot, and we were officially funded.

We then hired “The Machine” (Engineer #2) and I moved in with him into an apartment in the Twin Peaks neighborhood of San Francisco, mostly so I could harass him into programming day and night. And as my two engineers built a beta version of our call center software, I started dialing for dollars and calling call center owners with the pitch and promise of something cheaper.

After what must have been more than 2,000 cold calls, I finally reached a receptive voice on the other line. Joe owned a small but successful call center in Provo, Utah. He called my bluff and said that he knew we didn’t have anything solid yet, but he trusted we could get it built — but it had to be half the price I quoted him.

And that’s the early lesson I learned about entrepreneurship, or maybe it was a lesson in America itself. That after so many rejections, I wanted to reject myself, but then found someone who would mail me a check for $40,000, even during a recession, because they were risk-taking business owners themselves.

It made me realize that America was a magical place for entrepreneurs. Even the clueless ones.

With that $40,000 check we hired my former boss from the discount brokerage firm, hired a sales rep from the call center startup that had been acquired by Cisco and the five of us went to work in a small office in Walnut Creek.

We started shipping Dell machines with a Dialogic telephony board inside loaded with our call center software. It wasn’t sexy, but it sustained us enough to hire a few more people and start growing.

Then one day, for some odd reason, I had another epiphany.

Instead of building software to load on cheap servers to sell like everyone else, why not build one “mega-server” that we host ourselves and let people rent the functionality over the web?

My former boss told me, “No, that’s stupid, that’s killing the Golden Goose.”

The engineers told me, “No, that’s going to be a pain in the ass to build.” They sent me all sorts of studies from reputable analysts showing that “ASPs” (the buzzword before it was replaced by “SaaS”) was not a profitable business model after all.

I said, “Guys, what’s the alternative? You want to be the low-cost leader for the rest of your lives hustling these shit-boxes?” I pointed to the growing pile of Dell boxes accumulating in our small office.

Arguing vehemently with them for a month, I realized that on-demand software services weren’t profitable because everyone had just tried to take traditional client-server software and host it themselves.

They hadn’t thought to build something that was truly multi-tenant, meaning building software that was solely designed to handle multiple clients and accounts as a service. That would be a critical advantage for us, if we could pull it off, as it was significantly less hardware to purchase and much easier to manage customer accounts.

But there was another problem. A handful of other startups in this space had collectively raised more than $100 million dollars, compared to our $150,000, and they were pulling ahead. Like, way ahead.

Then one day The Machine gave me a Voice Over IP telephony box to play with. We both loved gadgets and we just thought it was so cool to be able to make long distance calls for free over the Internet.

And that’s when my Eureka 2.0 moment hit me — our competitors had single-tenant solutions requiring massive amounts of hardware and operational support to service customers at scale, but they also had to double their customers’ long distance bills.

Because a SaaS call center product has to have three phone connections ongoing per each call center agent (versus the traditional two in an on-premise model), it ate into much of the cost savings a customer would experience moving to SaaS. A service based on Voice Over IP would give us another tremendous advantage in the marketplace, as customers could actually lower their phone bills.

Few others were thinking about multi-tenancy and Voice Over IP, but I was finally starting to buy clues. And I had the good fortune of Tooter, The Machine and my former boss eventually rallying around my vision with their considerable super powers. To this day, I’m so thankful for each of them.

That “fateful day” for me was at a Safeway grocery store (where I would often worry about my debit card bouncing) when The Machine called me on my BlackBerry.

“Dude, dude, dude. Guess where I’m calling from?” The Machine asked.

“Uh, our apartment?” I started reading the cover of People magazine in the checkout line. Brittany Spears was dating someone new.

“Yeah,” said The Machine excitedly, “but this is the first call I’m making from our Voice Over IP stack. Sounds fucking good, right?”

I dropped to my knees, literally floored. We faced so many obstacles still, I knew that, but at that moment, and for the first time ever, I felt supremely confident that we were going to crush it. The competitors, the doubters, everyone. We were going to destroy the industry, then reinvent it in our own image.

And that’s really how the curve in our hockey stick began. We finally figured out a way to deliver a product that was 10x better and 5x cheaper.

That Safeway Express Checkout line where I got our first Voice Over IP call reminded me of that scene in The Shawshank Redemption where the main character crawls through miles of sewage pipe before finally being able to break free.

Shortly afterwards, we officially launched (built a new website) “The Virtual Call Center” and our business kept growing at an increasingly rapid pace. Our competitors, most of whom had not replied to my previous emails asking if I could buy them lunch in the city, were suddenly stunned at how low our prices were.

Ironically, we did end up being the low-cost leader, something we could do because our intrinsic costs were so much lower. We got substantial VC funding from great firms who believed in us and, finally, a great office space that impressed everyone except my father  — who kept asking me why I wasn’t a doctor yet.

The first year we had done $0 in revenues, the next year $900,000 and the next year $3 million. I led the company to $10 million in annually recurring revenues before I departed.  The truth was, the company had become its own entity and didn’t need me anymore.

Today, the company I named Five9 is traded on the NASDAQ stock market and employs hundreds of Bay Area Californians, with an IPO that gave the company an opening day valuation of $350 million dollars. Whenever I call into a corporation’s call center that’s using my software, I can’t help but smile. Until I’m on hold for longer than two minutes.

I’m not sure if I have any sage advice for other entrepreneurs, but out of this experience I did learn one important truth. Namely, you don’t have to be an Ivy League graduate (I’m not) or have a lot of money (we didn’t). You just have to believe in yourself against all reasonable logic, as trite as that sounds.

Believe that even if you do something stupid like quit your job without a clue, somehow you’re going to figure it out. Believe that after enduring years of the prison-like toil entrepreneurial life can be, you will emerge from miles of sewage pipes to feel the rain wash the crap off your face.

And that you will disappear to a beach in Mexico with a bag full of money, meet up with your co-conspirators and have margaritas.

More TechCrunch

Avendus, the top investment bank for venture deals in India, confirmed on Wednesday it is looking to raise up to $350 million for its new private equity fund.  The new…

Avendus, India’s top venture advisor, confirms it’s looking to raise a $350 million fund

China has closed a third state-backed investment fund to bolster its semiconductor industry and reduce reliance on other nations, both for using and for manufacturing wafers — prioritizing what is…

China’s $47B semiconductor fund puts chip sovereignty front and center

Apple’s annual list of what it considers the best and most innovative software available on its platform is turning its attention to the little guy.

Apple’s Design Awards nominees highlight indies and startups, largely ignore AI (except for Arc)

The spyware maker’s founder, Bryan Fleming, said pcTattletale is “out of business and completely done,” following a data breach.

Spyware maker pcTattletale says it’s ‘out of business’ and shuts down after data breach

AI models are always surprising us, not just in what they can do, but what they can’t, and why. An interesting new behavior is both superficial and revealing about these…

AI models have favorite numbers, because they think they’re people

On Friday, Pal Kovacs was listening to the long-awaited new album from rock and metal giants Bring Me The Horizon when he noticed a strange sound at the end of…

Rock band’s hidden hacking-themed website gets hacked

Jan Leike, a leading AI researcher who earlier this month resigned from OpenAI before publicly criticizing the company’s approach to AI safety, has joined OpenAI rival Anthropic to lead a…

Anthropic hires former OpenAI safety lead to head up new team

Welcome to TechCrunch Fintech! This week, we’re looking at the long-term implications of Synapse’s bankruptcy on the fintech sector, Majority’s impressive ARR milestone, and more!  To get a roundup of…

The demise of BaaS fintech Synapse could derail the funding prospects for other startups in the space

YouTube’s free Playables don’t directly challenge the app store model or break Apple’s rules. However, they do compete with the App Store’s free games.

YouTube’s free games catalog ‘Playables’ rolls out to all users

Featured Article

A comprehensive list of 2024 tech layoffs

The tech layoff wave is still going strong in 2024. Following significant workforce reductions in 2022 and 2023, this year has already seen 60,000 job cuts across 254 companies, according to independent layoffs tracker Layoffs.fyi. Companies like Tesla, Amazon, Google, TikTok, Snap and Microsoft have conducted sizable layoffs in the first months of 2024. Smaller-sized…

11 hours ago
A comprehensive list of 2024 tech layoffs

OpenAI has formed a new committee to oversee “critical” safety and security decisions related to the company’s projects and operations. But, in a move that’s sure to raise the ire…

OpenAI’s new safety committee is made up of all insiders

Time is running out for tech enthusiasts and entrepreneurs to secure their early-bird tickets for TechCrunch Disrupt 2024! With only four days left until the May 31 deadline, now is…

Early bird gets the savings — 4 days left for Disrupt sale

AI may not be up to the task of replacing Google Search just yet, but it can be useful in more specific contexts — including handling the drudgery that comes…

Skej’s AI meeting scheduling assistant works like adding an EA to your email

Faircado has built a browser extension that suggests pre-owned alternatives for ecommerce listings.

Faircado raises $3M to nudge people to buy pre-owned goods

Tumblr, the blogging site acquired twice, is launching its “Communities” feature in open beta, the Tumblr Labs division has announced. The feature offers a dedicated space for users to connect…

Tumblr launches its semi-private Communities in open beta

Remittances from workers in the U.S. to their families and friends in Latin America amounted to $155 billion in 2023. With such a huge opportunity, banks, money transfer companies, retailers,…

Félix Pago raises $15.5 million to help Latino workers send money home via WhatsApp

Google said today it’s adding new AI-powered features such as a writing assistant and a wallpaper creator and providing easy access to Gemini chatbot to its Chromebook Plus line of…

Google adds AI-powered features to Chromebook

The dynamic duo behind the Grammy Award–winning music group the Chainsmokers, Alex Pall and Drew Taggart, are set to bring their entrepreneurial expertise to TechCrunch Disrupt 2024. Known for their…

The Chainsmokers light up Disrupt 2024

The deal will give LumApps a big nest egg to make acquisitions and scale its business.

LumApps, the French ‘intranet super app,’ sells majority stake to Bridgepoint in a $650M deal

Featured Article

More neobanks are becoming mobile networks — and Nubank wants a piece of the action

Nubank is taking its first tentative steps into the mobile network realm, as the NYSE-traded Brazilian neobank rolls out an eSIM (embedded SIM) service for travelers. The service will give customers access to 10GB of free roaming internet in more than 40 countries without having to switch out their own existing physical SIM card or…

18 hours ago
More neobanks are becoming mobile networks — and Nubank wants a piece of the action

Infra.Market, an Indian startup that helps construction and real estate firms procure materials, has raised $50M from MARS Unicorn Fund.

MARS doubles down on India’s Infra.Market with new $50M investment

Small operations can lose customers by not offering financing, something the Berlin-based startup wants to change.

Cloover wants to speed solar adoption by helping installers finance new sales

India’s Adani Group is in discussions to venture into digital payments and e-commerce, according to a report.

Adani looks to battle Reliance, Walmart in India’s e-commerce, payments race, report says

Ledger, a French startup mostly known for its secure crypto hardware wallets, has started shipping new wallets nearly 18 months after announcing the latest Ledger Stax devices. The updated wallet…

Ledger starts shipping its high-end hardware crypto wallet

A data protection taskforce that’s spent over a year considering how the European Union’s data protection rulebook applies to OpenAI’s viral chatbot, ChatGPT, reported preliminary conclusions Friday. The top-line takeaway…

EU’s ChatGPT taskforce offers first look at detangling the AI chatbot’s privacy compliance

Here’s a shoutout to LatAm early-stage startup founders! We want YOU to apply for the Startup Battlefield 200 at TechCrunch Disrupt 2024. But you’d better hurry — time is running…

LatAm startups: Apply to Startup Battlefield 200

The countdown to early-bird savings for TechCrunch Disrupt, taking place October 28–30 in San Francisco, continues. You have just five days left to save up to $800 on the price…

5 days left to get your early-bird Disrupt passes

Venture investment into Spanish startups also held up quite well, with €2.2 billion raised across some 850 funding rounds.

Spanish startups reached €100 billion in aggregate value last year

Featured Article

Onyx Motorbikes was in trouble — and then its 37-year-old owner died

James Khatiblou, the owner and CEO of Onyx Motorbikes, was watching his e-bike startup fall apart.  Onyx was being evicted from its warehouse in El Segundo, near Los Angeles. The company’s unpaid bills were stacking up. Its chief operating officer had abruptly resigned. A shipment of around 100 CTY2 dirt bikes from Chinese supplier Suzhou…

2 days ago
Onyx Motorbikes was in trouble — and then its 37-year-old owner died

Featured Article

Iyo thinks its GenAI earbuds can succeed where Humane and Rabbit stumbled

Iyo represents a third form factor in the push to deliver standalone generative AI devices: Bluetooth earbuds.

2 days ago
Iyo thinks its GenAI earbuds can succeed where Humane and Rabbit stumbled