From waitress to CTO in 9 years

I wanted to share my story with this community because I truly believe that if I was able to forge this path for myself, literally anyone can.I started my career off as a life insurance salesperson. It was pretty much the first job I could get out of college, and I liked the idea of wearing a fancy suit and being in a fancy building and appearing fancy to all of my friends. The downside, which I hadn't considered, was that I simply do not thrive as a salesperson. I wasn’t having fun and I wasn’t making very many sales. I felt lost, stupid, and miserable and I quit after 9 months. I was living in NYC at the time, and as I left my office with no plan or job, I decided to apply at every restaurant along my walk home. I had no waitressing experience but eventually got a job at a lunch spot on the Upper West Side.I was super embarrassed that I had “failed” in my corporate job, and between my waitressing shifts I spent a lot of time trying to figure out what to do next. I was inspired by Grey’s Anatomy (lol) to look into pre-med programs, but had just missed all the application deadlines. I decided that I would learn a little ruby in the meantime, in case I wanted to use my imaginary future degree to get into biomedical engineering. At this point in time, I had ZERO understanding of computer science, or coding. I had taken a single intro-level CS class in college, in which I asked the professor to explain what an algorithm even was. She told me if I had to ask that question, then I wasn’t cut out to be an engineer, and to stop wasting her time. I dropped the class.As I was scouring the internet for coding resources, I stumbled upon Chris Pines’ ‘Learn to Program’, which explained how to open a terminal window, and what that even meant. It broke down the process into tiny, bite-sized chunks, and I was able to take small steps in my learning.As I was bumbling along, trying to come up with a plan, a friend of mine told me about a program called Dev Bootcamp. This was in 2013, when coding bootcamps were a brand new concept. I applied on a whim and got in! I wrote the check with what little money I had, crossed my fingers that it wasn’t a scam, and left all familiarity and comfort behind to fly up to San Francisco. I had never been there before. I stayed in a teeny tiny hostel for the 3 month program, cried every day because of how hard it was, and learned a lot. I remember being introduced to the concept of Classes, and instantiating instances of a Class, and Class methods versus instance methods, and not understanding the difference. It made no sense to me WHY we would ever have to use something like a Class, anyways. It freaked me out that I wasn’t instantly grasping these concepts -- did this mean I was destined to fail? Was I making a huge mistake? Had I been brought up my whole life thinking I was smart, but actually I was just stupid?Before bootcamp, I had never even considered that the tech industry was something I could be a part of. Further, I had never even heard of many tech industry concepts. Like, what is a product manager? What’s the difference between a static website and a web app? What is a startup? What does it mean to fundraise? What is an API? Literally, I knew nothing. It made me feel even more lost.I graduated bootcamp by the skin of my teeth, and started my job hunt. My resume looked like this: 9 months of sales experience, 1 year of waitressing experience, and that’s it. I knew I wouldn’t be landing a job based on my pedigree, so I had to think of a scrappier approach. My single saving grace was that I felt immune to rejection -- I had been rejected day after day selling life insurance, so a little embarrassment didn’t scare me. I began scouring the landing pages of startups, looking for tiny implementation bugs. Once I found the bug, I would guess the email address of the founder (usually [email protected], at the time), and cold-email them with my proposed solution. Miraculously, this approach worked, and I landed a job within the month.I was elated, but terrified. What if they found out that I didn’t know anything about coding? Was it possible that I had tricked them into hiring me during the interview process? To top it all off, I was so broke that I couldn’t afford a deposit on an apartment. With nowhere to live, I sheepishly asked if I could live in the office for a week or two (WITH MY DOG) until payday. They said yes!I spent 2.5 years at this startup, and look back on this time so fondly. At the time I felt like a walking disaster, but the doubt, hardship, camaraderie, mentorship, and friendship I experienced during these years set the baseline for who I am today. I received outsized mentorship, autonomy, and trust. I discovered that engineering is not a boolean thing that you either can or can’t do -- it’s a skill that gets honed over years and years, through trial and error and mistakes. The biggest secret of all is that no one really knows what they’re doing. It was such a relief to arrive at this conclusion.That startup later went on to get acquired by Spotify.In 2016 I began looking for a new challenge, and landed an engineering job at Reddit! There were about 60 employees total when I joined, so I had the opportunity to make a real impact. I spent the next 5 years on various teams, doing all kinds of cool stuff. I was a core contributor to the Reddit redesign, I became a senior developer, I began managing a client-side infrastructure team, and then two teams. The thing I’m most proud of is the internal engineering development program I founded (called GAINS,, which I created to boost opportunities (and by way of that, salaries) of underrepresented groups at Reddit. I was also able to speak on one of the big stages at Grace Hopper in 2019. I grew up at Reddit, both personally and professionally, and couldn’t have asked for a better experience.As a seasoned developer, I began thinking about what I wanted to do with my life. The idea of starting my own company had always seemed like an impossibility. I had never known or interacted with a founder who looked like me, so it never occurred to me that founding a company was something I could do. At the same time, I remember thinking that the founders of Airbnb, Slack, and Lyft, etc. were so lucky. Those founders were in the right place at the right time, and opportunity just landed in their lap! No risk involved -- instant success! I wished I could be so lucky.In the summer of 2020 I got a text from a buddy of mine that had worked with me at my first job -- the startup I mentioned earlier. He said “I’m starting a company, and I want you to be my CTO”. I decided to humor him; to hear him out. Turns out, he had one hell of an idea. We kicked around the idea for 6 months, running through various product iterations and monetization strategies. We interviewed over 80 people to collect user research. Months of due diligence later, and DwellWell ( was born. Turns out, we weren’t the only ones who thought it was a great idea; we were able to raise 560% of our initial fundraising goal in 3 months. It dawned on me that the founders of Airbnb, Slack and Lyft, etc. weren’t simply lucky. They had taken a chance on themselves -- one that might not work out, a SCARY chance -- and with that commitment were able to build something great.My cofounder and I were able to leave our full time jobs in January 2021, and went all-in on DwellWell. I’m running our technology org and product development, and could not be more thrilled. We have an all-female engineering team, we’ve launched our MVP to a private beta, and raised enough money to start hiring a larger team. I’m dedicated to hiring with diversity at the forefront. You can’t build an app for everyone, when everyone isn’t represented within your company.I wanted to tell this story for those who are scared. Those scared of leaving their jobs to pursue engineering. Those scared of being a junior developer, because what if you fail? Those scared of taking a risk and starting your own company, or joining an exciting startup right at its beginnings. If I can do it, any and all of you can, too.
Love this, thanks for sharing your story! I joined the DwellWell waitlist, excited to learn more about it. I’m def in your marketing persona. :)
I am so thrilled to hear that! Will let you in ASAP :)
What a unique and wonderful story, @samanthacarow, thanks for sharing!
Thanks so much for your kind note :)
What. a. story. Thank you Samantha for sharing!
Thank you! I'm so happy this is resonating with the community :)
Thank you for sharing your story!I’m buying a home in January and definitely joined the waitlist. Looking forward to seeing your hard work in action.
Thanks for your support Natalie! Will let you into the beta ASAP :)As we're still in private beta, the experience is ... very beta-like! We're making rapid improvements and developing partnerships so you should be good to go in January.
Totally feel it! If you need user feedback, just let me know! Happy to contribute. Planning on checking it out this week. Thanks for letting me join the beta.
Thank you for sharing your story Samantha. This has inspired me so much.
I'm so glad to hear it!
Wow! What an inspirational story — truly truthful and a deep-dive in grit. At times, when I am reading your experiences, they are insightful as they mirror some of my tech insecurities. Thank you x 10k for sharing your life experiences and congrats to your CTO role and funded startup! A💜heart for your courageous endeavors!
Thanks so much Anne!
So happy to hear about your success! Thank you for sharing the whole journey (and not just the shiny destination). The details and examples really help - like showing exactly how uninformed or broke you were.. cause some times the reader will be like "ok but clearly it's not that bad" or otherwise not know how to relate / situate themselves..I do think your original "luck" perspective still has merit though. For sure there is grit and risk-taking, but there is always some luck I think! Anyway congrats again and all the best :D
Thank you so much!
Thank you for sharing your story - you are courageous (something I am still learning for myself). Now I need to go check out DwellWell.
Yes! Come check us out :)
Wow what an amazing story, and such a fantastic example of how mindset really is everything (rather than "luck" or even "talent") - thanks so much for sharing!
Thank you!!
Thank you for sharing this @samanthacarow! Would be so honored to have you add your journey to the 1000 of unique life paths on OwnTrail ( to further inspire women and help them embrace their non-linear paths!
Oh wow what an interesting site! I'm heads down until we're out of private beta on DwellWell, but will explore after that!
Such an amazing story, @samanthacarow! Your struggles are so relatable and your resilience is inspiring
Thank you!
You hav no idea how badly I needed to hear such story right now. Thank you for sharing it!
I'm so glad!! Thank you
I love this story so much! Thank you for sharing, @samanthacarow!
Thank you!
WOW inspirational story! Thank you so much for sharing @samanthacarow! Added myself to the waitlist too :)
Thanks Jenny!
WOWWW I am bookmarking this so I can re-read whenever I have self doubt as a recent engineering bootcamp grad <3 THANK YOU!!
Thank you! I promise it gets so much better after you land your first eng job.
What a wonderful story. Kudos to your resilience and not giving up on YOURSELF. Thanks for sharing :).
Thank you!!
Thank you for sharing your story! For those who were in a similar position to @samanthacarow : Hi! I'm Rachel Serwetz, an ICF-certified career coach. My background is at Goldman Sachs & Bridgewater Associates, before moving into the career space to systematize my novel career exploration and job search methods and tools.My mission in life is to ensure people feel supported in making these critical, impactful career decisions. These decisions can feel stressful and tough, but with the right support (which you deserve), you can feel relieved, excited and confident in your next steps. I have been coaching hundreds of professionals for over 8 years and have developed unique processes and frameworks so that you can confidently clarify your ideal career direction and efficiently job search to land a role you feel fulfilled by. Happy to chat directly and see how I can help! Best,
@samanthacarow, thank you for sharing the gritty details of your story! This is amazing and definitely a jolt of inspiration that I need. CTO - wow.!!!!! I'm inspired by your tenacity, vulnerability, scrappiness, and resilience!
Thanks so much!!
I’d love to recruit for your company
Thanks for sharing @samanthacarow, this was super helpful and thoroughly inspiring. Congratulations on your launch! How's the startup life going? I wish you more wins
Thanks @olubukolaobakin!! Things are going great -- we're now a mighty team of 9 :) and educating homebuyers on the daily!
Awesome! @samanthacarow Good job on product hunt as well! :)
Wow! Your story is extremely inspiring and something I can totally relate to!! I bartended my way through college and was never certain about which path to take afterwards. I now have 1 year of professional work experience as a Junior Developer and I am so excited for what's next! Thank you so much for sharing @samanthacarow .
I'm so glad you can relate!! Isn't it crazy what a difference a year can make in your career? It's only the beginning for you -- can't wait to see what you achieve!