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A Bootstrapped Startup’s 4 Year Anniversary Reflections & Learnings

Rachel Serwetz
Rachel Serwetz
November 17, 2021
A Bootstrapped Startup’s 4 Year Anniversary Reflections & Learnings

The day I was accepted to NYU Stern’s Tech MBA program, I started my company.

Let me take you back. After working for 4 years in the corporate world, I left my job at a hedge fund, and then had been floundering for months. I was unemployed, being pushed & encouraged to interview for jobs that mirrored the last job I had had even though nothing I was applying for excited me. I just kept going after that simple, straight lined path because there was no one helping me broaden my horizons, think about what I truly cared about, and open up the creative avenues to find where I might be excited to go next in the professional world.

So, after about 5 months of job search misery, I landed a corporate role that was pretty straight and narrow. After two months, it was clear it wasn’t a fit, for various reasons, but this all was inevitable. When you’re in a job that isn’t a fit (i.e. either role, industry, and/or environment are not aligned), you either:

  1. stick it out and manage to be successful enough that the company lets you stick it out, all the while hating it, or
  2. you hate it enough that you eventually quit, or
  3. you’re in such a poorly fit role that you don’t perform and are let go

All in all, I believe that being in a role you’re not a fit for is a waste of everyone’s time and at such an emotional expense that no individual deserves to endure. We’ve come to know that being in a role that isn’t a fit for you is the norm, and I’m here to tell you it doesn’t have to be that way. But back to the story.

I left that role shortly after starting, crying on the phone with my Dad telling him “I can’t do it anymore.” I had felt unspoken pressure to be in a 9-to-5 job when I knew that entrepreneurship was really the path I needed to go down. That was the path that was meant for me, but it was also a scary, risky path. That level of risk was so scary to me that it delayed my start in pursuing the path I knew I was meant to do, until it was clear I couldn’t fake it any longer in the corporate world.

Weirdly enough, I was accepted to NYU Stern’s Tech MBA program on November 16th, 2017, the very day after I left that last role. It was strange timing, and such a blessing in disguise. Finally, I had the confidence to pursue the (scary) path I knew I should — starting my own company.

This doesn’t mean that I think every new entrepreneur needs a Masters degree to start their company (definitely not), but for me, it helped feel like a fall back plan, just in case the company didn’t work out. I don’t think that’s the best way to go about it necessarily, but at the time, that acceptance gave me the umph to rip the bandaid off and start. Starting is always the hardest part.

So here’s what I’ve learned in 4 years:

Knowing yourself is key. How you are will affect your decisions and your outcomes. You can definitely grow and evolve, but eliciting self reflection often and improving your self awareness is key to ensuring you don’t get in your company’s way.

  • Your hard skills — While you may not have time on your side to learn every skill you need before starting a company, you should figure out what hard skills, knowledge, and exposure you need as a bare minimum to be able to hire properly, develop a quality offering, and market it efficiently and effectively. Figure out how to hire the right team and/or get advisory/mentorship to fill in your gaps of knowledge and see around the corners.
  • Your soft skills — Whether you’re really personable or not, whether you’re really direct or not, whether you’re really efficient or not, insert any key trait or skill here and that will impact your company. You’ll want/need to hire people who both complement and align with your key values and affinities. I created our culture document & assessments way too late in the game! Do this sooner than you feel you need to, to ensure you not only hire for a person’s skill set, but also, considering their approach to work.
  • Your tendencies — I’m super impatient — this plays into my decision making. I’m also really structured and systematic. “What I’m like” will involve strengths and weaknesses. Sometimes these “ways of being” can be helpful in certain ways or a hindrance in other ways. For example, impatience can mean that I’m scrappy and creative, but it can also mean that I rush to make decisions. Arguably, many people would say that in a startup, deciding things more quickly than not is better anyway.
  • Side note & additional learning → The hardest balance to find is between efficiency and quality. Figure out where you fall on the perfectionist scale and always consider the time involved in a decision relative to how big that decision is.
  • Your mindset — The stories you tell yourself, your assumptions, your subconscious or conscious beliefs, are critical. Whether you feel capable and deserving of growing a large company. Whether you feel confident in your expertise enough to build a robust strategy, to trust yourself, and to follow it through to execution. Any mindset limitation can trip you up. Your key is to acknowledge it as quickly as you can (versus learning the hard way when it manifests into your actions), grab it by the horns, grapple with it, unravel it, resolve it or guardrail against it.
  • Everything evolves. It feels like every 3–6 months it’s a whole new company, a whole new challenge. This requires me to rise to the next level and push us to the next level.
  • There is a constant balance between zooming out and zooming in. 95% of the time feels like you’re zoomed in, but you must create and protect time to zoom out and reflect on the overall approach. (Monthly metrics/learnings meetings help)
  • Bootstrapping is a crazy journey. Being a solo founder is a crazy journey. Being a first time founder is a crazy journey. Without resources, you have to figure out how to grow. It can make you really creative, or really stressed. Without a partner and without having done this before, you have to find guidance, mentorship, and trust in yourself.
  • The requirement of comfort with ambiguity is a given; better yet, you’re #1 job will be to figure out how to easily create order out of chaos.
  • Your level of interest in the problem you’re working to solve, your ginormous vision, the demand/opportunity that exists, and your early proof points of success are the only things that will enable resilience and persistence on this difficult, crazy journey. Ensure you’re genuinely aligned with what you’re doing before you begin.
  • Learning how to hire well is critical and worth the time investment. Don’t skimp on it. Your people are there to help drive your outcomes, or lack thereof.
  • Most people won’t understand the journey; find other entrepreneurs to connect with.
  • I’m proud and grateful looking back to see how far we’ve come, but I’ll forever be driven by how far there is to go (and all our continuous ideas to enhance our support of every professional with every career decision).

There’s been a lot more nuanced learnings about specific business-oriented functions, but above are my most “zoomed out” reflections on the journey so far. This path is weird and wild. As much as it’s stressful, I feel 100% certain that I am doing what I’m meant to be doing, and I’d never replace that.

A Bootstrapped Startup’s 4 Year Anniversary Reflections & Learnings

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Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4.5+ years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has served as a Career Coach through the Flatiron School, Columbia University, WeWork, and Project Activate.

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