I left my corporate at Amazon to build from scratch. It didn’t go as well I hoped.
At Amazon, frankly, I was lucky on timing and opportunity. At 23, after a stint at a wobbly startup, I didn’t have the skills, prestige, or experience to position myself, but I felt lucky when the recruiter let me know I was offered a position. I started as a scrappy, unbelievably green Business Analyst at the most entry-level, and I was given a combination of trusting leaders, growing organizations, and new opportunities to prove myself. I was positioned to launch new programs, build real-time operations technologies, and grow a team. I did have natural abilities of consensus-building, I could understand incentives and goals spanning different organizations, but I also possessed rebel instincts to point out where the current state didn’t match the ambitions of the company. I like applying my interest of economics into the product I was buiding. I was good at my job.
But it wasn’t my dream. I wanted the prestige of raising venture capital, and being on some podcast talking about the amazing business I built. Like a Travis Kalanick, a scrappy founder who surprised everyone and became a titan of industry. And deeply, I didn’t want to be at the whims of top-down organizational directives and layoffs, and I was tired of spending so much time reading tea-leaves out of existential protection for the team I managed. I had a date picked for when I’d quit, had been telling my wife for months the date I would resign.
I didn’t have a plan if I truly think about it. I knew Supply Chains, including Amazon, struggled with cyclical spikes in oil prices, weather events, labor shortages: weekly financial reviews with executives always had these 4-6 callouts of unforecasted issues that would take 4-6 weeks to normalize. I wanted to start there, and start reaching out on Linkedin to find people in my network who were in Operations outside of Amazon. Then, I proded about disruptions in their business. Do weather issues happen? How did you respond to tarriffs? Pretty much leading people in my network and teeing up the problem for them on calls. I spent months trying to prove to others that it was a real problem, and during customer discovery calls I found a few companies that had disruptions impact their business.
Lesson 1: Amazon’s Problems aren’t Everyone’s Problems
I had operated in a world at Amazon, working in the most sophisticated supply chain in the world. But so many of the problems were niche problems that other companies probably wouldn’t have ranked as their top problem. When you get so big, you have different problems. The nature of the problems expand.
I found a disruptions that existed. Sure, weather events disrupt a region for 3-5 days. But in reality was something that came up every couple of months and felt more like big paper cut to them. They had all sorts of bigger problems like how to balance their volumes across 3PLs and Transportation, which Shipper to Use and When. But their operating costs were already tight, and they already paid vendors for other products. And disruptions impact higher speed supply chains more, and most businesses don’t need to ship on the same day. They didn’t care if a shipment showed up a couple of hours late, they cared if the package was multiple days late or damaged and ate into it every week.
As I clammered around and followed up on customer discovery calls, I started for feel like I was yelling in the sky, alone, trying to prove a problem existing for customers who weren’t in Amazon. And my idea to solve it was right of our 2017 techland: a SaaS product as a mission control to help planning teams identify and account for these risks. I was so focussed on convincing investors, any investor, that it was a problem worth solving, with an uninspired, vague technology to address it. I needed to be honest: did I have an idea to solve a structural, burning problem, or was a tech guy trying to rollout some vague notion of AI in Supply Chain?
Lesson 2: You Can’t Force a Co-Founder Fit
I could feel myself stumbling. I was nervous I was going to fail without getting anything of the ground. My self-confidence was degrading too.
I would watch Y Combinator VCs on Youtube over coffee after my wife when to work. Find your co-founder first. It’s the hardest thing to find and the biggest risk to any startup succeeding.
So, I went looking for a Co-Founder, and who was maybe onto a legible business. I came into an also awesome startup community in Seattle, Foundations, but I went looking for a Co-Founder mostly. I didn’t want to be stuck in the world of thinking, without ever building, selling, and growing a business. I didn’t quit to think about a business, I wanted to be building one.
And I found someone. I found someone with a customer in home services, and I liked his technical background from a FAANG company, and a high level it looked like a legible team. Non-technical co-founder meets technical founder in a fragmented market. Market seemed fine. Not exactly operations, but it checked a box. I was starting a business.
I never worked with him, or felt personally accountable to him previously. We had no proven chemistry and ability to challenge each other. I was not motivated to work together personally. I made it like a professional relationship, even though it should have been someone I’m personally connected to.
Lesson 3: Passion for the Problem
I had followed my Co-Founder into a problem that didn’t inspire me. The goal, helping independent businesses grow, was virtuous. The problem we were solving was mostly an SEO problem. Get more reviews, update Google Maps, building AI generated websites with SEO optimized job content.
I didn’t care about SEO. I’m not interested in how to use keywords to improve Search data. I’m not drawn to allocating Ad Dollars to someone else’s Ads. Why was I the right guy to solve this problem again?
And I burned myself out. After thousands of cold calls, forty demos, six paying customers, and I felt empty. The things I read about over the weekend about markets and international affairs had no connection to some problem which I was supposed to be passionate about. Why did I have the right to build a special business?
Lesson 4: You Pick Where You Sell
Every market has its own unique way of selling. Customer from within your personal network are the strongest. Then you move to Linkedin, Email, Socials, and Paid Channels. You need a few customers at scale to prove yourself.
I had no one to email, I didn’t know a single owner of a plumbing or HVAC business. And home services businesses don’t spend a lot of time on Linkedin, and all of them already have “someone who helps with marketing”. Either externally or internally. We needed to talk to customers and get them to trust us. And these businesses grow with personal trust primarily. We had no trust. We looked at other companies in the space, and we realized some had a strong Cold Call Motion or had connections to large Private Equity firms. We had no connections. It was time to cold call.
Ten thousand cold calls for a problem I kind of understood, with a technology where I could vaguely help, is a recipe for burnout. I didn’t understand how we differentiated ourselves, and didn’t understand our product differentiation. SEO isn’t a determinative problem, you try to follow a template and look at web date every week. I didn’t see the big results in the data, and I didn’t really intuitively know I started to feel like an imposter.
In a sales motion I hated, and a problem I wasn’t passionate about, I was at a dead end. I parted ways with my Co-Founder and sold him back the small business we had after 12 months. After growing my career for 9 years uninterrupted, I was lost, sad, and alone.
I’m not totally out of it yet. I want to find something that caters to my edge. How do users interact with technology? How can using AI actually benefit them in the real world, without making them pessimistic about what happening to their job? Which products are businesses are geniunely good for the world, and how can I solve it at scale? Do I enjoy doing what I do during the day?