My name is Josh Clawson and I am the founder and CEO of Ox — a generative AI platform for scaling job training and coaching. 

I’ve had a lifelong interest in the problems people are faced with in job training. I watched a lot of people I really care about struggle with last-mile job training. 

As automation and AI came into the world, I had a hypothesis that we could use that to tackle the problem that I've been focused on. 

We last raised a pre-seed round of $1.5M at a $10M cap in March 2022.

It was a long journey to that point. We started the company in 2019 and focused on building our first MVP, which was video chat. 

We set out to fundraise in Q1 2020, but COVID put a virtual end to pre-revenue fundraising for a while.

We focused on bootstrapping through 2 more MVPs and pivots before we settled on integrating AI into an enterprise focused product.

We had finally reached a point where we felt we had product market fit because we had a few enterprise customers who we had done a proof of concept for that were converting to paying customers. 

We set our target team size, an ARR target of $1M in the next 18 months, and backed into the runway we would need to achieve that.

We did not anticipate inflation becoming a factor so we wish we had raised more.

We wanted to hire the first few members of the core team, had an ARR milestone we needed to hit, and needed to find enterprise design partners who shared our vision.

We had the MVP, but we needed to design and build the finished product with scale in mind.

We wanted to know that we were aligned on our vision for the future. We had the tech stack, we had the talent to build the company, and knew we could execute. 

We wanted our investors to believe in the power of AI to make a meaningful impact. 

More importantly we wanted to work with investors who actually understood early stage investing rather than a more conservative investor who was looking at the early stages for deal competition reasons.

I was a first-time founder, so I wanted them to be comfortable with that as well. 

Partnering with an investor who was comfortable with that and had built before was key. 

I would research the partners at a firm that could be a good fit. I would try to find the partner we wanted to work with and would be married to for 10 years or more. 

From there I would work backwards to finding a warm connection. 

We would use reciprocity — helping another founder friend out, then asking for an intro. That was always the first route we would take. 

The second route was to write investors cold by filling out a form on their site. 

We would try to make it stand out, but also made sure not to share so much that it took away from the magic of the first meeting.

We also had some luck at AI-focused events. 

We had over 350 pitches that led to 2 lead investors and around 10 angel investors.

The traction was ultimately what did it for us. Before the traction, investors were more skeptical that customers would pay for it. 

As soon as we got the traction from 2 enterprises that shared our vision, things really unlocked for us.

Early on the pitch was a problem-solution style pitch. We now use more of a ‘why now?’ story arc.

We also demonstrated our fanatical commitment to solving this problem. 

We stuck with it and bootstrapped it for several years before we were able to raise money — they liked our dedication.

We had a couple angels trickle in, but then we had a sizable supporter get really excited.

We initially set our fundraising amount much lower than what we ended up getting.

We decided if we filled out the round, we’d have more time to validate, but if we oversubscribe, then that would also work. We ended up filling out that whole round.

We really just kept folks in the loop as it filled up and momentum built naturally.

Inflation was a big problem. By Q4 2022 the value of what we raised in Q1 was worth 25% less. 

Between our vendors raising their prices, the rising cost of talent, and the literal value of the dollar decreasing, it felt like the amount we’d raised was worth a lot less.

We also dealt with the transition from zero interest rates to non-zero, which further added pressure.

We obviously don’t have solutions to the macro economic markets, but these were probably the biggest challenges.

We were raising in the middle of the crypto trend in venture markets - early to mid 2022. 

Almost every pitch meeting we went to started with them asking if we could integrate crypto into our product.

The meeting would start, and we would tell our story about job training and AI, and they would ask where crypto fits in. 

When we said that we didn’t incorporate crypto, they asked if we would consider it — it was a wild time. 

Make sure that you're obsessed with the problem you're aiming to solve. You might be building towards solving that problem for a decade.

Also find team members who share your vision — you will have a long-term commitment with them as well.

Building a community of founders was one of the best things that I did. Having a community of other founders to help each other through is really critical. 

There are certain things you can't tell your parents or your partner because it will scare them.

You also can’t share everything with your stakeholders because you have to set them at ease that you are in control and on top of everything. 

Other founders can be a great group to share war stories with and vent to.

Two books I like are The Mom Test and The Messy Middle.