Sapa, Vietnam (pre-startup life)

Lessons From My First 6 Months As A Founder

Last year, I started Uplevel, a concierge that matches you with a personal development coach. Now, Uplevel has over 40 coaches and has successfully matched 45 people with a top-tier coach.

While I’m still early in my journey, I’ve already been on a rollercoaster of emotions and challenges. I’ve been anxious about putting myself out there. I’ve felt overwhelmed by tackling too many things at once. And as I coach and chat with fellow early-stage founders, I notice the same patterns come up. We experience many of the same mindsets and behaviors that hold us back.

When I reflect on what’s helped me make the most progress, I have 3 key takeaways:

  1. Follow up, persistently and shamelessly
  2. Focus, focus, focus
  3. Find people who believe in you more than you believe in yourself

It boils down to managing 3 things well: relationships, time, and emotions.

While each journey is unique, I believe these lessons apply to all founders. By writing up my learnings, I aim to reinforce them for myself. Hopefully this can also help other early-stage founders.

Follow up, persistently and shamelessly

We live in a world full of distractions, notification fatigue and email overload. Have you ever missed an email? You’re not alone. This happens all the time, and as email senders, we can’t take it personally.

There are a million reasons why someone didn’t respond to your email: They didn’t see it. They read it while on the go and forgot to respond later. They haven’t yet had time to give it ample thought. (Just to name a few!)

People love to ignore emails. (

It can feel unnatural and pushy to follow up, but this is standard practice in sales. If people aren’t interested they can ask you to stop. But often people appreciate the followup.

Example: One user said she wanted to reconnect in a month after returning from traveling. So I followed up in a month, and didn’t hear back for two weeks. I followed up again, and once more 5 days after that. I started to think she wasn’t interested anymore and my emails were clogging her inbox. Finally she booked time and we chatted. At the end of the call, she said:

“Hey Jen — I want to let you know that I Iike talking to you, because I have to think about what I want to do. Typically that goes to the back of my mind. When you ping me and I talk to you, it makes me think about things in the long term.”

This user matched with a great coach through Uplevel. Three months later, she reported greater confidence and a stronger sense of self. Had it not been for my followups, she would not have experienced this impact.

That’s when I realized: my follow-ups aren’t annoying; they are valuable. I stopped thinking about follow-ups as spam, and started reframing them as gifts. Ever since, it’s been easier to be persistent and shameless.

Sometimes it helps to be creative when following up. Email isn’t for everyone; some prefer text messages or calls (and are way more responsive to them!). Others prefer in-person meetings. Once, after a woman rescheduled a call 6 times, I suggested we meet up for coffee near her office. She agreed. Right before our meeting, I asked a close mutual friend to ping her about it. Lo and behold, she did not flake this time!

Focus, focus, focus

Focus is critical on a macro and micro level. On a macro level, a business is more defensible if it solves one problem well vs. ten problems mediocrely. On a micro level, founders must focus on driving the business forward when they have limited runway. This seems obvious, yet it’s so easy to get distracted in the age of the attention economy.

The “Canada Principle” from Netflix’s early days shows how powerful focus can be. It stems from their decision not to expand to Canada. Despite it seeming easy and profitable in the short term, it would likely distract the team from long-term growth. This principle drove critical decisions that laid the foundation for Netflix’s success. For example, they shut down their profitable DVD sales business to focus on their long-term bet of DVD rentals.

When choosing how to spend your time, remember opportunity cost: saying “yes” to one thing means saying “no” to a thousand other things.

YCombinator’s ethos is that startup founders should focus on 2 things: 1) Build product and 2) Talk to users. Anything else is “fake progress”, and in fact a distraction:

Slide 9 of Adora Cheung’s Startup School lecture on How to Prioritize Your Time

A personal anecdote: A month or two into full-time work on Uplevel, a friend presented me with a part-time contract opportunity. It seemed well-paid and interesting, but unclear whether it would take 3 or 15 hours/week. At a point where I was mentally adjusting to zero income, the opportunity for extra cash was tempting.

I consulted a fellow founder, and he reminded me of the opportunity cost. He encouraged me to get clear on my runway, set time-bound goals, and determine at what point I must work for someone else.

I took his advice and set a goal of matching 20 people with coaches by the end of the year. To achieve this, I had to say no to the contracting opportunity. I also said no to exploring tangential ideas, e.g. group coaching (applying the “Canada Principle”). Once I buckled down and channeled all my energy towards 20 matches, I surprised myself. I hit my goal with two weeks left in the year.

Find people who believe in you more than you believe in yourself

YC partner Michael Seibel once tweeted advice for startup founders that included this:

Michael Seibel’s advice based on seeing 1000 startups go through YC

I will acknowledge this now: starting a company is HARD, and I feel bad a lot. (Indeed, the highs are high and lows are low — especially during a global pandemic!)

My founder friends inspire and support me on a regular basis. Founder communities like the On Deck Fellowship provide solidarity and encouragement.

Non-founders provide support, too. Julie Zhuo, VP of Design at Facebook, describes her confidence-boosting friend Annette:

If you don’t think you deserve to win, or doubt you have what it takes to make it happen, success will slip through your fingers like water.

Annette made it her job to help those around her feel that confidence. She saw you for what you were — superpowers, angsts, warts and all — and she believed in you. I was on the receiving end of her powerful belief time and again, and I am so grateful to her for that. When someone believes in you that fiercely, you can’t help but believe a little more in yourself.

Annette reminds me of my coach. My coach believes in me more than I believe in myself. Not only that, but she brings awareness to negative thought patterns that hold me back. My coach is a neutral sounding board. She helps me see tough situations from fresh perspectives. Then she gives me clarity and confidence to move forward.

Last week, I experienced a wave of self-doubt. I turned to my coach, who helped me step out of myself and see the bigger picture. I was absorbed in Me and Myself, while external factors were affecting my state of mind. She normalized my experience — many of her clients have been feeling this way lately.

Whether it’s a coach, therapist, friends, cofounders, or an SO, a support squad makes a huge difference. (If you want to find the right coach but don’t have time to search, check out Uplevel!) While I’m still early in my journey, I doubt I would have made it this far had it not been for my personal cheerleaders.

It’s been a wild ride so far, and I’m just getting started. One of the most rewarding parts of starting a company is the continuous learning and growth.

People appreciate when you follow up, as long as you’re providing value. Greater focus leads to greater results. Starting a company is hard, but a strong support network helps sustain morale.

These learnings seem rudimentary. But they’re easy to forget amid the barrage of tasks, relationships, and emotions founders must manage every day.

What are the biggest lessons you’ve learned on your journey?

Thanks to Shreya, George Xing, Julian Weisser, Vance Roush, James Gallagher, and David Lee for reading drafts of this.