Starting a Business With Someone You’ve Never Met

One of the most important decisions you can make when starting a business is to choose a co-founder who compliments you, to help you achieve your goals. 

Growing up, I always dreamed of being my own boss, but it was serving in the military that finally gave me the nudge I needed. Like so many of my peers, I succumbed to one of the biggest clichés of being in the Army — I became tired of being told what to do, where to be, and what to wear. The endless bureaucracy wasn’t for me. I wanted to bet on myself and chart my own path. I was driven to be my own boss.

My vision was to start a software company. Having studied entrepreneurship in college, and worked in Silicon Valley, the path of least resistance was to build a software company. The margins were incredible, and software businesses can scale indefinitely. Or so I was told. 

Out of college I worked for a venture-backed startup and became jaded by the pressure. Corners were regularly cut to appease investors, and people were cut loose on a whim. It felt very transactional. I wanted to do things my way. Early on, I decided I would try to build the company I wanted to work for. This would be a company that wasn't cutthroat, that focused on long-term outcomes, and most importantly, one that didn't take on venture capital.

The idea of starting a business is sexy. You noodle on business names and think about how great it’s all going to be. People will love what you built, and your inbox will overflow with all of the demand. At least, that’s the impression I had.

Right out of the gate, I hit snag after snag. I didn't have any money, and I didn't know how to code. So, I started to learn. I stayed up until the wee hours debugging code and poring through documentation. 

Most of my early days of entrepreneurship were bogged down in minutiae. I spent more time vetting documents with lawyers or stuck on hold with a banker than I did building a business. Even worse, prospects couldn’t care less about what I was trying to build, and no one was beating down my door asking for business. Not even close.

By day I was working as an operations director at a startup, and by night I was building one. And I was doing it all by myself. Entrepreneurship is lonely, and the task list is never ending. I had no one to bounce ideas off of. No one to collaborate with. 

I set out to build a tool that tracked when leads and contacts changed jobs, and to surface these changes to sales reps through Salesforce. I was solving a problem I’d experienced when I was a rep, and that I knew others faced as well.

In addition to trying to start a software business, I started moonlighting as a freelance Salesforce admin. I was essentially helping friends who were sales leaders at companies that lacked someone with CRM expertise. I’d put in a few hours each night to help them out, but didn’t take it very seriously. 

Then one day my life changed, and I didn’t even know it. Another entrepreneur named Kenny came into my life asking for help.

He was an Operations Manager at a fast-growing company. His story almost perfectly mirrored mine: he was a former Sales Rep who was forced into operations. And with no clue how to build out a Salesforce org, he was in over his head. A mutual acquaintance introduced us, and we were off to the races.

Working with Kenny as a customer felt like a breath of fresh air. I had worked with many businesses over my first two years as a Salesforce freelancer, but he was the first person who, I felt, spoke the same language as me. What he lacked in domain expertise (though I wasn’t far ahead of him), he made up for with vim and vigor. 

At first, Kenny was just a client, but without either of us really noticing, our conversations always ran long. He showed up to every meeting with new challenges and naive solutions. His excitement was infectious. Working with Kenny didn’t feel like work because both of us were learning new things every day. He would occasionally ask me, as the consultant his company was paying, to let him do the work, so he could internalize what we’d done and start to understand how to fish for himself.

Then one day, out of the blue, he sent me an email asking if we could set aside some time to talk. He was thinking of stepping out on his own and was looking for any work that could pay the bills until he got his software business up and running. He and I had a good working relationship, so he figured I might kick him some work here and there. 

Part of me was excited. Working with someone else who didn’t think what I was doing was insane was like a breath of fresh air. On the other hand, I had to ask myself, "What does he bring to the table that I don’t already have?"

The answer was obvious. He brought me time. Whether he was capable of doing work I was doing wasn't a question anymore —  I'd watched him do it day in and day out for the past year. So I told him, "Sure." And I gave him everything I hated doing: cleaning up spreadsheets, digging through messy databases, and all the other tedious tasks I loathed.

But his energy and excitement never wavered. He was online before I was, reading documentation and proposing solutions. He worked as late as me, despite being three time zones ahead. I can't count the number of calls we had past midnight, my time. 

As his skillset (and my client base) expanded, I began giving him more complex projects and tasks. I started letting him run calls with customers, but I was still there as a backstop in case he got in over his head. I noticed, though, that I was stepping in less and less. His questions got more sophisticated, along with solutions he proposed. Clients were praising him regularly, and he handled issues with grace. 

All of our business came through referrals and word-of-mouth and was focused primarily on tactical admin work. The business had grown, but was essentially a great lifestyle business. My goal was to focus on my software product, rather than build a consulting business, but Kenny saw things differently. He sensed product-market fit and wanted to go all-in on the Salesforce consulting market — he asked me to hop on another call, which turned out to be yet another unexpected turning point in my life. Kenny proposed we start a new, joint venture together as Salesforce consulting partners.

I was immediately skeptical, but also willing to hear him out. His idea was to become “official” partners with Salesforce, which would allow them to refer business to us (Salesforce needs good partners in order to help their own customers succeed). He had built relationships with dozens of Salesforce reps in Toronto and noticed a common complaint: they couldn’t find good partners. Kenny recognized how happy our customers were, and was confident that we could offer value through a new way of approaching Salesforce consulting. If we did this well, his contacts would send us business.

By the end of our call, I was convinced. 

Our wives, on the other hand, were more skeptical. My wife and I had just had our first child, and we were thinking of a second. Kenny’s wife assumed I would steal the company from underneath him, while my wife couldn't believe that I was crazy enough to start a business with a person I'd never actually met and who didn’t even live in the same country!

But after collaborating with him for more than two years, I had no reservations about Kenny. Not only was he smart and driven, but he had connections that I didn't. He was strong where I was weak, and vice versa.

But at this point, details start to matter. Not only the logistics, such as where the business is created and what we call it, but also sticking points like who makes the decisions and what's the split?

I leaned on advisors for their recommendations, and every single one of them told me either a) this is a bad idea, don’t do it, or b) give him no more than 10% of the company, and only if he earned into it over 2-4 years. 

That didn’t sit right with me, though. I saw things differently.

If the shoe were on the other foot, I wouldn’t want to take a tiny minority stake in a company that was supposed to be a “partnership.” If we were real partners, then his success was my success. This thing had to be 50/50, or else there could be resentment.

So, I ignored my advisors and did what felt right. Kenny, expecting me to offer him a small fraction of the company, came to our call prepared to negotiate. But I said straight out of the gate that it made the most sense for us to split this thing 50/50 — there was no need for negotiation. He said “hell yes," and we were off.

From that moment on, we were inseparable. We spent thousands of hours collaborating, debating, and reaching consensus. And there’s never been a single moment where I doubted him as a partner. 

Fast forward to 2020. We had been Salesforce partners for only a few months when COVID-19 hit. Like everyone else, we were very unsure about how a global pandemic would affect both our company and the handful of early employees who were taking a chance on an unproven business. Initially, things were OK, but then we had a stroke of good fortune. One of the first customers Salesforce brought to us manufactured ventilators and was in a bind due to sudden, skyrocketing demand. They had orders from every hospital in the world and didn’t have their systems prepared to support such an influx, so we were brought in to the right the ship. We passed our first test with flying colors, and business began to pour in.

Typically, lots of demand is a good thing for a growing business. Unfortunately, as a bootstrapped business, we could only grow as quickly as we could collect on our receivables. Although we were in heavy demand, we were reinvesting every dollar back into growth. And then our biggest customer decided they were not going to pay their invoice. Nor were they going to pay their past due invoices. 

Kenny and I looked at our bank balances daily, and at any given moment we had only a few days worth of cash available. For our biggest customer to stiff us on that much money meant one of two things: 1) we were about to miss payroll (something I couldn’t imagine) or 2) we weren’t going to be able to pay ourselves until we got the company back on solid footing.

Both of us knew right away that the first option wasn’t really a choice. So we went with option two. Those days were full of stress and fear, but what we learned during that time changed how we operated the business going forward. For one, no more customers were going to leave us over the barrel on invoices. Ever. Second, we were going to hire a finance person immediately so this situation never happened again. Third, we would be diligent about maintaining a rainy day fund so that we never had to be faced with the question of whether or not to pay the team. 

In 2022, we brought our (100% remote) company together in person for the first time for a team-building retreat. By this point, Kenny had been asking to manage more and more of the company. When we started Kicksaw, Kenny managed Sales while I oversaw Delivery and the back office. But over time, he started to take on more responsibilities. Delivery eventually moved onto his plate, in addition to Sales and Account Management. Shortly before our company retreat, I proposed to him that he be named CEO. We made the big announcement in front of the Kicksaw folks who’d helped us achieve our success as a business, and we’ve never looked back.

I sometimes look back on what my entrepreneurial journey would be like if Kenny had not come into my life. Where would I, and Kicksaw, be now? Would there even be a Kicksaw?

His background was dramatically different than mine, and he brought different perspectives to our discussions when we were considering going into business together. But at the same time, we really aren't all that different. Sure, he was an Israeli immigrant to Canada who’d lived in Toronto his entire life, while I was a kid from a small logging town in Oregon (and also the child of an immigrant). But we both learned early on in life that hard work was the only way to succeed. Neither of us had a trust fund or a backup plan. We both paid our own ways through college and have had to fight for everything we have.

While I can’t say so for certain, I do know for sure I wouldn't have created a company as successful as Kicksaw without Kenny.

I often describe having the right partner as not a 1+1=2 relationship, but more along the lines of 1+1=10. Having a person who you trust implicitly, who you can confide in, and who understands the position you’re in and will give you the hard feedback you need, as a peer, is invaluable. These days, when I hear of a solo founder gutting it out alone, I think back to the earliest days when I thought I could do everything myself. I was misguided then. I was also naive. 

Back when Kenny and I first met, I’d never scaled a business before. Nor had I ever brought on a business partner. I had ideas of what a business partner could/should look like, but I had no expertise in finding or vetting a potential cofounder. What I’ve learned since then is that this decision to go with Kenny as a partner is the most important decision I’ve made in the entire history of Kicksaw. 

Recently, Kenny and I did a personality assessment for the first time in our lives. At our company retreat this year, we ran DiSC assessments across the entire organization. These assessments outline personality traits, communication styles, and other things that make us who we are. It was surprising (and not really surprising) to discover that Kenny’s personality was almost diametrically opposed to mine. I was labeled dominant, persuasive, a fast mover, and results-oriented, while he was pegged as modest, patient, reflective, and thoughtful. It was another great example of how unlikely, but perfectly balanced our partnership has been.

To wrap this up, my advice to aspiring entrepreneurs is to find a partner who will match and compliment you. They should match your drive and energy. They should have a similar vision and work ethic to you. But ideally, they should come from a different background, and have a different temperament from you. Though we’ve disagreed on countless topics, Kenny and I have never had a disagreement we couldn’t talk through, and that’s been yet another key to our success, and to Kicksaw’s success. 

Don’t go it alone — you’re not a hero. Find that ideal partner. Then go create something amazing.