From startup to BigCo and back again

Why I decided to leave my Fortune 500 job to join a startup.

From startup to BigCo and back again

"If I'm being honest, 'startup' scares me to death," a former colleague told me shortly after I started my new job at a two-year-old venture-backed company. His fear is not unfounded. It's widely known that most startups fail, and that is a real risk whether you're starting or joining one. But his fear is also a prime example of the perceived safety of employment at an established company without acknowledging the potential tradeoffs.

Prior to 2018, I had never worked at a BigCo. In fact, I had never worked full-time for a company I hadn't co-founded. So it surprised those who knew me when I went to work for an innovation group within multinational corporation Procter & Gamble, exactly one month after my last startup had shutdown. What most people didn't know is that my decision to work at a Fortune 500 company after being an entrepreneur my entire adult life was driven by both necessity and curiosity.

When my own company became part of the 90% startup failure rate statistic, I needed a new job to support my growing family. With a then two-year-old son and another child on the way, I could not afford to start over. And after six years as a founder, I needed a hiatus from entrepreneurship. Having little experience as an employee, I knew it would be an adjustment for me. Nevertheless, I decided that the best way for me to recover from failure was to play it safe by getting a job rather than creating a new one.

By working at one of the world's largest companies, I hoped to accomplish several goals. First and foremost, I wanted to provide for my family. As a startup founder and CEO, I was paid a salary of ~$40K/year (if I was paid at all), had no 401(k), and put everything I had back into the company. I was 33 years old when the company was dissolved, and I had no savings or retirement. I was not in a position to start another company and I worried that a Cincinnati startup would not pay well enough to get us on track to financial security.

I never planned to retire from a BigCo, though. I hoped that I would discover an unsolved problem or unmet need in the market while working at a Fortune 500, like the founders of VNDLY did when they realized enterprises needed a better way to manage vendors. I thought that if I worked at a BigCo long enough, I would be exposed to glaring inefficiencies and costly problems, meet my future cofounder(s), and ultimately start another company to commercialize a solution that we validated while still earning a salary.

I also wanted to learn as much as possible, such as how to be a better manager; how to influence others when I wasn't the decision maker; how established companies made build vs. buy decisions; and how senior executives led large organizations. Learn and earn, right? Since I had never worked for a BigCo before, I wanted to gain that experience firsthand and confirm whether my own assumptions about corporate America were true.

Spoiler alert: Many of them were true.

The work-life imbalance

Before I worked at a Fortune 500 company, I thought having a '9 to 5 job' meant the employee worked roughly 40 hours per week. When the whistle blew at 5 PM, you went home to have dinner with your family like Fred Flintstone. To my surprise, I found that I frequently worked more as a Fortune 500 employee than I did at a startup!

From calls at 7 AM about that week's dumpster fire to meetings scheduled over lunchtime to emails with URGENT in the subject at 9 PM, this was the norm during my time at a BigCo. It was also the example set by many of our leaders, making it the seemingly unwritten expectation if you wanted a promotion. The shift to remote work during the pandemic only made it worse, with Zoom calls consuming every hour of the day.

The pervasive hustle culture has led to the false assumption that startups demand employees to work insane hours, like the legend that a team at Apple in the early 1980s worked 90 hours per week and loved it. But in my experience, this is only ever true in short bursts. If a startup expects to attract and retain top talent in 2021, flexible working arrangements are a requirement to succeed.

Meanwhile, I know salaried BigCo people who regularly work after business hours and on weekends. It doesn't have to be crazy at work.

The job security myth

In the three short years that I worked at two of the world's largest companies, my colleagues and I were impacted by multiple reorganizations. These corporate restructuring events are typically managed by an outside consulting firm and branded as a 'transformation' or some other term to make them more palatable to staff, but the fact is they often result in layoffs.

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To be clear, I do believe these changes are often necessary to ensure the continued growth and success of the broader business for shareholders, especially at larger enterprises. But if they're communicated and executed as poorly as those I experienced, it can result in months of uncertainty for employees. While your parents or grandparents may have retired after 40 years at one company, this type of job security is increasingly uncommon even at the largest companies.

So while startups are undoubtedly risky, at a BigCo you're only one reorganization away from needing a new job. There are few careers without such risk today.

The pervasive lack of focus

A skill that I honed as a startup founder was context switching – the ability to jump between tasks during the work day without losing productivity. On any given day I could pitch investors, conduct interviews, collaborate with my team on key product decisions, and more, without losing steam. I never imagined that this would aid me at a BigCo.

As a Senior Product Manager for a Fortune 500 product management organization, I would devote four weeks of the year to planning Objectives & Key Results (OKRs). The problem was not the amount of time this planning took, it was the fact that few teams were actually able to adhere to their plans during the quarter due to an organization-wide lack of focus.

OKRs are designed to Measure What Matters, but if you change what matters in the middle of a quarter, then the outcome will not be great. Sometimes, an unexpected event occurs that forces a rapid change in priorities – such as the COVID-19 pandemic. But this cannot be the norm. OKRs are ineffective if the company does not have consistent and measurable priorities for teams to execute.

The constrained resources of a startup force focus and foster creative thinking in a way that is difficult to replicate within the confines of a BigCo.

For the most part, I accomplished my goals during my time at Procter & Gamble and The Kroger Co. I was well-compensated which helped my wife and I to pay-off debt, buy a larger house for our family, and start saving for retirement. I met dozens of people smarter than me – some of which I'd love to start a company with or even hire someday. And I learned a tremendous amount about how large, publicly-traded companies operate. There were many valuable lessons, but I increasingly felt like there was something missing.

At a startup, I could make a decision and face the consequences – good or bad. I had the autonomy to do that because speed matters more than perfection.

At a BigCo, I had to schedule a meeting to discuss the matter, determine who the decision-makers were, and then gain their approval before I could act.

At a startup, my compensation and progression were directly tied to my performance. If I wanted more, I simply worked to make it happen.

At a BigCo, I needed to wait an arbitrary amount of time before I could be promoted or earn more. My fate was determined in a calibration meeting.

At a startup, lack of focus kills. Time invested in one area of the business is at the expense of another.

At a BigCo, being busy is often a badge of honor. Every quarter is full of initiatives that are often started but rarely finished.

The longer I worked at a BigCo, the more frustrated I became. I despised the red tape, the cultural fear of failure, the politically-motivated behavior, and most of all, the adherence to the status quo. I increasingly felt like I didn't belong – a cog in the machine – and worried I had stopped progressing in my field. I thought that if I could just be promoted to a product leadership role, I might be better able to effect the change I thought the company needed to serve its customers.

So I decided to set a personal deadline: I would be promoted to Group Product Manager by October 31, 2020. If that didn't happen, then I would resign. To demonstrate my potential and value to senior leadership, I poured myself into work. I volunteered for assignments others didn't want. I mentored my direct reports to deliver incredible results (and they did). I evangelized the importance of data, experimentation, and OKRs in a product-led organization.

I repeatedly shared my progress and plans with my direct manager, but it either fell on deaf ears or they didn't have the authority to fully support my ambitions.

After being laterally moved to a new role during the second reorganization I was impacted by in just three years, and offered little guidance on how to advance my career within the company, I resigned. January 14, 2021 was my last day at a BigCo. I sacrificed an unvested equity grant valued at $12K and a more than ~$20K cash bonus to join a startup as one its first 100 employees. I could not be happier with my decision.

If you've considered working at a startup, or perhaps even starting your own business, know that it's not as scary as it may seem. If you join an early stage company at the right time in its growth trajectory, it's very likely you'll earn a competitive salary with great benefits and even greater work-life harmony. It's true that most startups fail, but there's no better way to learn than to be part of a team that creates something new together.

Even the world's largest companies started with a founder, a vision, and a group of people willing to take a chance on both.

Although I've joined another startup instead of founding my own company, I'm closer to entrepreneurship which has reignited my passion for building new businesses. In my role as the General Manager at Fast, I'm navigating the ambiguity of an early stage company while directly supporting the effort to bring an innovative product to a global market. I'm learning more, earning more, and moving faster. For the first time in years, I feel like I belong.

P.S. Fast is hiring.