Year 2 Startup Learnings
Learning and unlearnings from building Plymouth Street
I’ve been building Plymouth Street for the past 2.5 years, and this is my attempt to share the journey. Overall, I feel incredibly lucky to work on something I deeply care about. I’m proud of the product and team we’ve built, and I’m the happiest I’ve ever been in my work life. That being said, the past year has been one of the most challenging periods of my life — both professionally and personally — and I’ve learned a lot from the experience.
Remember to have fun. Building a company is ridiculously hard. The odds are stacked against you, and there’s a good chance you’ll fail and have nothing to show for it. Sometimes it’s so hard it’s actually funny (oh, we need to 10x revenue this year? Sure, no problem!). Remember to laugh.
Develop an attentive mind. I currently meditate daily (about 10 minutes each morning) and practice yoga. These are powerful tools for cultivating mental clarity and self-awareness. I’ve noticed that when I prioritize this practice, I feel calmer in high-stakes situations, and I’m better at making thoughtful decisions. For instance, I’m quicker to notice my emotional state during a tough meeting, which helps me respond more effectively rather than react impulsively.
Trusting intuition. More than ever before, I’ve found myself leaning into my intuition — a “gut feeling” — about every part of the business, especially hiring. Vibes matter. If you get a strong feeling about someone, pay attention to it. Of course, data and diligence are important, but there’s a lot to be said for trusting your instinct of whether a person or decision is aligned with you.
Embrace the uncertainty. There are so many things you don’t know as a founder— lean into that. Learn to enjoy the learning process itself. I like to think of it as playing a game: the fun is in the act of playing and the discovery.
Lead with compassion (for yourself and others). If you’ve been an A-grade student your whole life, starting a company might be the first time you fail spectacularly at almost everything. From trouble setting up payroll to pivoting product strategies, it can be painfully humbling. I’ve often been my own harshest critic, which is exhausting. Being kind to yourself makes it easier to be kind to others —and that builds a healthier, more supportive environment for everyone on the team.
Work as an act of service. Choose your customers wisely. I spent almost a year building a carbon-removal startup before realizing it wasn’t the right fit. That experience taught me that the path we serve (and the people we serve) profoundly shapes our day-to-day. If your work doesn’t feel aligned with your core values, the startup grind can become draining very quickly.
Collaborate with people of high integrity. Relationships are tested when things get tough. Working with honest, accountable, and respectful people keeps the company culture strong. Conversely, partnering with those who lack integrity can erode trust and lead to dysfunction—no matter how talented or connected they may be.
Take your work seriously, but don’t take yourself seriously. When you start achieving some success, you might get invited to speak at events or podcasts, investors may start knocking on your door, and prominent people in tech will reach out to meet you. Those things can be shiny and exciting, but they’re not the true measure of success. Keep your ego in check and focus on doing great work.
Be the founder, not just “play” the founder. There’s a difference between being a founder (focusing on substance, product, and people) and playing the founder (focusing on vanity metrics, networking events, and external validation). Real success comes from building something meaningful — something that solves a problem — rather than chasing superficial milestones.
Learn to say no. When I worked in VC, it was part of my job to attend industry events, network constantly, and schedule regular coffee chats. Now, I have to be extremely disciplined about what I commit to. Twice a month, I audit my calendar to see which activities are valuable and which aren’t. Time is your most precious resource — protect it fiercely.
Take time off. For the first two years, I worked non-stop and came close to burning out. That wasn’t good for me or the company. My energy levels set the tone for everyone else. Based on Elad Gil’s advice, I aim for 3 day-weekend once a quarter and a whole week off once a year.
Finding a renewed love of fiction. A funny and unexpected joy of starting a company was rediscovering my love of fiction. By the end of long, intense days, I found TV too stimulating (no more screen time, please!). So, I turned to novels to unwind. Some favorites from last year:
Never Let Me Go by Kazuo Ishiguro: Although I disliked the low-agency protagonist, I loved the nostalgic imagery of the British countryside.
High Fidelity by Nick Hornby: Witty and entertaining, it’s a perfect wind-down read for music lovers.
Klara and the Sun by Kazuo Ishiguro: A thoughtful exploration of AI, loneliness, and what it means to be human.
Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin: A beautiful look at friendship, creativity, and the worlds we build — real and virtual.
And some tactical productivity hacks (that worked for me!):
Daily to-do list: I physically write a to-do list every morning, then map it onto my calendar. My calendar is my single source of truth.
Morning deep work: I do my best thinking in the morning and can only manage a few hours of deep, focused work each day. I’m extremely protective of that time.
Afternoon logistics: For more tactical tasks (answering emails, scheduling, paperwork), I save the afternoons.
Chatbot brainstorming: I use AI chatbots (Claude, ChatGPT) to workshop ideas. Pro tip: explicitly ask them not to be sycophantic so you get genuine feedback.
Pomodoro technique: I often do 25–40 minutes of deep-focus work, followed by a 5-minute break.
Stay hydrated: It sounds basic, but it’s important — your brain is about 75% water, so even mild dehydration affects cognition.
Progress over perfection: Projects are iterative. Small steps each day build momentum.
Spend time planning: I’ve underestimated the importance of planning in the past, and I’m trying to be more intentional about it now.
Thanks for reading!
This was great!