How can bootstrapped founders reach PMF?

How a rejection was an eye-opener for our startup!

As a first-time founder, it might be rare to come across someone who has it all figured out and is moving at a fast pace, failing quickly and moving on to the next item - all while being scrappy, hustling, trying multiple avenues to research and launch their audience and product respectively.

At least, I can say I fell into the category of someone who was treading very carefully and wanting to bring the best world-in-class product out there. It's not that I did not speak to customers. It's not that I did not speak to the right customers. It is that I did not speak to enough customers and I did not ask them the right questions - until it was a bit late.

My co-founder and I first got the idea to build a product like GEXPR 2 years ago. But we only began working on it one year ago. Our problem statement was pretty clear to us - accessing experts is too difficult if you want to reach out to someone to get quick advice on a topic - you spend too much time watching videos and reading lengthy blogs! A quick face-to-face conversation is much easier, quicker and gets you the personalised response you need.

We started digging a bit deeper and found that multiple use-cases could be applied to this problem - consultants, subject matter experts, content creators - they could all be an expert on our marketplace and give advice to users.

Of course, thankfully, we realised rather quickly that we needed a focussed and specific target audience and after a lot of customer discovery and interviews we came to the conclusion that prospective students who want to apply to higher-ed institutions struggle to connect with recent grads and alumni to get first-hand advice about a school or course. Social media DMs and finding "someone who knows someone" doesn't cut it. That's why we started narrowing down on this audience to give them a directory of alumni available to talk to 1:1.

With a bootstrapped approach we had to find efficient and cost-effective ways to approach our audience and get sign ups once our MVP was ready in December 2021. We got in our friends and family members who cheered on us and sent us all the love and best wishes. (One of the most crucial things a founder can have is a strong support system and I am more than grateful for the hype squad I get to rely on each day!)

Fast forward to May 2022, our user base had been growing at a reasonable pace with organic, word-of-mouth marketing working and users referring others to join our marketplace. Great! Maybe we're ready to take this up a notch?!

I began approaching accelerators, mentors, investors and other networks to get on to the next step and quickly move forward with their support. I even got a response from some startup experts who invited us to present our idea and product for a potential investment and access to their ecosystem. I was thrilled with how things were going and really felt ready to take the plunge!

It wasn't until the second meeting was over, that we heard back from the team with a rejection. I wasn't mad or upset, I was just disappointed. I have faced a lot of rejection when I was doing fundraising for a non-profit (believe it or not people are less likely to give you money if it's just for a good cause and doesn't give a certain ROI)! I even faced a lot of rejection job hunting when I first moved to USA and had all the visa restrictions possible. Rejection is commonplace.

What disappointed me was how I wish I had done a lot more, a lot sooner. I read the book "The Mom Test" a bit too late in the day. I "hustled" to find scrappy ways to reach my target audience by simply sitting at my computer. I spoke to all the right people to guide and direct me to master this important meeting pitch and in the process, lost track and focus of the product and users. It was a real hit in the gut to know that I had let a lot of things go off my radar.

For starters, I was so focussed on MoM growth of users, I did not even look at retention. When I did look at some amount of retention figures, I did not even understand cohort based retention. I had no idea what the users wanted most.
Secondly, once I did understand retention, I had completely missed the big picture of how I would increase the LTV of the users. Thirdly, I had been "talking" to a lot of customers but instead of getting out of the building and finding them, I was waiting for them to respond to my messages on Slack.

In the 6 weeks of going from almost getting funded to getting rejected I learned so much about the importance of not standing too close to the elephant (idea).
I wasn't attached to the product or the idea, but I wasn't married to the user either. Because I did not know the user's journey well enough to propose, yet!

After sulking for a full evening, I got back to it and here are some things I did:

I did something I never imagined doing again - I attended campus tours of top universities in NYC to meet prospective students and interview them.
I built multiple landing pages to A/B test what the audiences resonated with and sent them a follow up form to ask them what they were looking for.
I got into scrappy mode and entered all kinds of Facebook groups, Telegram and Discord channels, sent DMs on social media and personally wrote to 100s of potential customers about what I am building. I actually got responses!
I drafted some newsletters inspired by some of the best content creators I have been following and sent them to the segmented audiences to see what they resonated with and if they'd be happy to get on a call.
I tested my hypothesis of who would be the paying customers by moving away from B2C and focussing on potential B2B clients who I could pilot with.

As confusing as this sounds, it is now beginning to put the full puzzle together for me. Instead of leading with product, I am leading with the users. But first, I am finding a good number of users whom I can share my product with and focussing on the multiple ways I can continue to provide value to them in the future. I will iterate the product based on discoveries and retention metrics.

What would be your advice for a first-time founder (bootstrapped) trying to increase user retention and finding product-market-fit?