Good is definitely the enemy of great.

Over the past decade, I have had a B2I EdTech company that has provided me a comfortable living without investors on my back, but for the life of me I cannot grow!

It was never my intention to create something big. I just wanted to live in the Caribbean, kitesurfing every day, and earn ~$4,000 per month without working too much.

My plan worked out and I spent a tremendous 10+ years living like a grasshopper, traveling the world, working a few hours a week and finally settling down in a beach house.

The problem began when I fell in love with a local girl... Her job was in finance for a hotel where she earned $400 a month, but she proved to be a math whiz. As she worked her way up in corporate America (online), within a couple of years of getting married, she got a job offer for a six-figure salary in Boston, where we bought a house and had a child.

While this may sound like a great story, my $4k/m has recently shrunk to $3k. I have lived a decent life on the island with that money but in Boston, I am struggling to get by. Over the last couple of years, I have been searching for ways to increase my revenue but to no avail, which is why I am seeking advice from this great community.

About my company

- EdTech / B2I (schools) / Online tutoring & OPM - We solve an important and interesting problem in our industry. - Excellent moat. Sophisticated software. - Very long sales cycle but very long contracts - 6 school partners (non-us) - 100% bootstrapped - 2 employees / full time, offshore (developers) - 0 growth / main problem: no established sales channel.

About me

White-male, 40+yo, non-English native. I grew up in a low middle class family in the middle of nowhere. My degree is from a community college. Needless to say, I am not part of any influential circles.

What I tried

1. VC / Angels The only way I could approach VC/Angels was by cold emails. A few third-tier investors responded. They liked our mission, business model, revenue, client's list… but we always failed their ultimate question, "who is your lead investor?". I felt that rather than having a genuine interest in the company they are considering, most seed investors hope that the founder will introduce them to more prominent investors. https://twitter.com/Jai__Malik/status/1351363787614523395?s=20

2. Boston seed stage I am aware that Boston is the 3rd startup hub but I soon realized that 90% of that money goes to MIT/Harvard founders and/or > Series A. Seed round for non-MIT/Harvard is close to non-existent.

3. Accelerators I interviewed for the TS, 500, and YC accelerators. They all rejected me. I’ve been accepted by 2nd tier accelerators but I spoke with previous founders who revealed that their entire cohort did not raise a single dollar.

4. Meetups Due to COVID, there are not many edtech meetups. Connecting with other founders did not produce any significant results.

5. Revenue share Not enough revenue.

What I think would work.

Our US competitors are all getting new contracts through RFPs. Each of these companies is well funded, so they hired a team of RFP experts. I participated in a few (it takes about 2 months) and lost them all to companies with inferior products, higher bids, but better presentations. RFP specialists are not motivated by equity from a bootstrapped startup. Even if they are very excited about the idea, they would not take a leap of faith.

...any advice?