Being the Boss vs. Working for the Boss Thoughts from the founding CEO of a 365-day-old startup

Exactly one year ago, I co-founded my startup. Before taking the entrepreneurial plunge, I spent my entire 20-year career working for other people on their ideas—from small nonprofits with a couple dozen people, to pre-launch startups requiring product scaling and team building, to well-established tech companies with tens of thousands of employees. I’ve bounced from LA to SF to LA to NYC and back to LA working on the next big thing.

Now at the one-year mark with my startup, I’m reflecting on the advantages of being the boss and building my own dream versus working for a boss and supporting someone else’s dream. And I won’t bury the lead: one isn’t better than the other. They both have their positives and negatives, and certainly working for a company has distinct advantages over going the entrepreneurial route. But, if you’re more driven by creativity like I am, at some point you just gotta take that leap.

Being the boss

It’s an emotional rollercoaster. Sure, there are highs and lows anywhere you work, but I’ve never experienced the pure confidence of world domination coming directly on the heels of debilitating doubt and uncertainty… and back again from one day to the next, or really, from hour to hour. With so much on the line, the pendulum of thoughts and feelings can be confusing and energy-zapping… which also adds to the sense of incredible pride and satisfaction. Go figure.

Work-life balance is a challenge. If there was ever a time to prioritize, this would be it. As the founder of a startup, I have to make decisions, compromises and sacrifices—especially on the home front. Dinner with friends? A vacation? A weekend off? It can be a challenge to do pretty much anything other than work, but it’s a proven fact that taking time off to decompress and rejuvenate makes you more productive and efficient. That’s why even though I’m hovered over my laptop on mornings, nights, and weekends, I also make conscious time for yoga, running, getting to the beach, and cooking good food.

I get to wear all the hats. At this stage, I’m the marketing department, the support department, people operations, finance, legal, and janitorial engineer. While for some people that might feel disjointed, chaotic and head-spinning, for me it’s probably the thing I love the most about being the boss.

It’s fun to dream big. My business partner and I started Reaction Commerce by dreaming first about the kind of culture in which we wanted to immerse ourselves. While it’s important to us that we also build a business that matters, foremost in our minds is the desire to create an environment that’s creative, inspiring, energizing, and challenging both personally and professionally. We want it all—a product that changes people’s lives and a company in which we can continue to grow and thrive for the next 20 years. At this point, the sky’s still the limit, and that’s really fun.

Creating new features feels awesome. We’re building an ecommerce platform from scratch, and we know that our progress will be measured in years, not months, yet every day feels like we take a step closer to accomplishing our dream. We’ve launched a ton of features in our first year, and each time we create something new and put it out there, it fills me with great pride and accomplishment. There’s still only three of us, which makes it all the more satisfying knowing we’re often able to do things that take large companies ten times as long. We’re moving at lightning speed, and I have to admit that it’s a bit addicting.

Life is about making a difference. Being the boss means I get to take a lot of meetings with potential clients, investors, and partners. It’s fun sharing our vision with other people and getting their valuable feedback. It’s even more fun forming alliances with people who share our vision. And most rewarding of all so far is that every person who’s heard our pitch has agreed that we’re solving an important problem for developers and businesses, and they’ve gotten excited about how we’re going about it. It’s rewarding to know that we’ll be making a difference.

Working for the boss

You get to wear fewer hats or maybe even only one hat. This isn’t true if you’re working for the boss in a smaller, earlier-stage startup, but if you’re at a larger, more established company, it’s usually more clear what’s expected of you, and the pace is often much slower. When I was starting out, both of these were huge advantages because I learned what my strengths and weaknesses are, and I developed my confidence. When I worked as the Sr. Director of Product & Operations at Citysearch, which is a part of InterActive Corp (IAC), initially I reported to a Citysearch SVP, who reported to the CEO of Citysearch, who reported to an SVP of local services at IAC, who reported to the CEO of IAC. Essentially, I was a manager in a large media company. My role was very defined over consumer and business products, and I had counterparts in every other major area of the business. Each quarter we had to prepare and present business reviews for IAC. I wore a only a couple hats and had to manage all the way up the chain in order to get almost anything of strategic importance done. This allowed me to find the best ways to collaborate with counterparts who had varying personalities as well as hone my skills in preparing and presenting what I felt would be most effective. I loved the challenge of it, but over time I realized how restricting that kind of environment became. Ultimately, I didn’t feel like I could affect the change I wanted.

You take fewer risks. While playing it safe can be stabilizing for a business and its employees, it can also lead to complacency. I’ve gravitated toward working for early-stage startups because I thrive on the excitement and the ability to innovate and take risks. But I’ve learned quickly that once you have existing customers, investors, revenue projections, and bills to pay, you start to get more cautious and operate in more calculated ways. This is sometimes called innovators dilemma. When I was brought in as a COO of an early-stage fashion ecommerce startup, the team was small and the business was in its infancy, but the company was part of a tech accelerator that had majority control and interest, and they were heavily involved in day-to-day operations. I was the COO, who reported to the CEO, who reported to a Partner at the accelerator, who reported to the CEO and founding partner. We had very little ability to take risks because, ultimately, the owners of the company called the shots and strategy. So, even in a startup, it’s important to assess the role and really understand who’s making the key decisions. As a creator, this experience was limiting, and we ended up recommending that the accelerator consolidate the business. I’ve learned that I want to do more than merely push pixels; I want push envelopes and disrupt industries.

There’s more bureaucracy. Ultimately, this is probably the biggest challenge for every growing business. There can be lots of people involved in decisions, which means that things can take longer and become political. Often there are top-down decisions being made where there’s very little transparency in what’s decided. If you disagree, you’re often stuck. When I joined Yahoo from the GeoCities acquisition, I definitely felt the shift in going from a startup-like culture to a large company. The first few years at Yahoo were incredible. It felt like each product line was it’s own startup, and because we were so free to create, we were able to craft a meaningful strategy and roadmap. The environment was electric—filled with possibility. But the company more than doubled in size during my tenure expanding to over 10,000 people, and in the last year or so, things got bogged down by bureaucracy. As the company grew, it was harder and harder to get things done. There were more people at the meetings, and instead of streamlining decisions, the inefficiencies became rampant. The approval process became insane as everyone jockeyed for position and started fearing for their jobs. Even though I enjoyed the people and I still found the work challenging, I started to feel more like a cog in a machine or a factory worker on an assembly line. And once I realized that I was losing passion for what I was doing, it was time to go.

There’s a safety net and a clear role. The biggest advantage in working for someone else is the safety net. There are often more benefits, and someone else worries about the lights, payroll, healthcare, etc. Working for a boss has meant that I know more about what the work rules are, I have a more clearly defined role, and my effort is both predictable and rewarded. I have found great comfort in working for someone else. My years at Yahoo and Citysearch were the perfect environments in which to learn. I got to focus on building the best user experiences, and I never had to worry about administrative details. When I joined Etsy as the VP of Product, it was still very early stage, but it was already mature in many aspects. By then, I knew how to pick the perfect job for me, and Etsy was it. We had already raised venture capital from top-tier investors; we had a Board to rival all Boards and I participated in every one of those meetings; I defined the product roadmap and strategy and reported directly to the CEO; I got to take numerous risks in a company that was on a crazy trajectory, and I loved just about every minute of my time in Brooklyn. Even though I wasn’t the boss, I was the head of my area, I enjoyed the clarity of my role, I was empowered to grow the product and the team, and I was working on a business that wasn’t just well loved, it was making a difference for millions of people. Those kinds of experiences are hard to come by, and I cherish that one. Now, I look forward to creating my own company that borrows from and mimics some of those fantastic positives.

So far, my experiences over the last 20 years have taught me that when I’m working for the boss, no matter what the size of the company, it’s possible to “lead from my seat.” I’ve learned that I can be the CEO of a product line within a larger company. I’ve learned how to maneuver through personalities and bureaucracies, and that when my role isn’t satisfying, I can craft it into something more meaningful. I’ve learned that working for someone else has distinct advantages and disadvantages. And I’ve especially learned that I’m ready to be the boss. So now, one year into it, I can’t imagine going back to working for the boss. Here’s to year two!