Today, Alex takes us to May 2019. 

His business had been going for 2 years. And at this particular time, they were in the midst of a rolling fundraising strategy. 

At seed level — this is not uncommon. Their product market fit was evolving and they were often pivoting between ideas. So they didn’t want to be tied down.

Alex’s business was based around a candidate platform that would act like LinkedIn for the commercial hire industry and collect data to help with the hiring process. 

He’d been a founder for 20 years at this moment. And had several times where he was close… But this time, he was definitely dealing with burnout. 

 He was

  • Doing 5-10 pitches a week
  • Heavily involved in the business
  • Covering for someone
  • Doing up to 15 screening calls in a day
  • Still answering investor questions

And all of this led to Alex waking up on a Saturday morning, unable to move. 

He recalls his emotions being all over the place. 

His world was too much, and he didn’t know if he could take it any further. 

It had gone too far.

Only after 3 weeks of rest, was Alex able to return to his role. But he’d have to approach it in a different way. 

What Led Alex to Dealing with Burnout?

Alex was basically doing 3 jobs at once. 

He had taken on a big challenge by raising money at seed level. 

And he was playing the waiting game with angel investors. The process was gruelling. It always is. 

Alex’s co-founder was kind of with him. But they had agreed that Alex would focus on fundraising while he stayed in product. 

So he felt like he was dealing with it alone. And worst of all, nothing was working. 

He was pitching his heart out, and didn’t believe the investors were interested in what they had. Which left him questioning the business. 

The market of 2-sided marketplaces was difficult. And what they wanted to build required a lot of marketing and investment to work.

Do you change your pitch to match what the investors are saying? 

Or do you keep going until you get an investor who understands you?

As it was Alex’s 6th business, there was more ego involved because he thought that it should be going better.

And therefore, he was telling everyone it was going well. 

As a result, he became tunnel-visioned. 

There was only 1 outcome, and that was getting the fundraising. In hindsight, they probably would have been okay whether or not they got the round.  

Essential Learnings From Going Through Burnout

Looking back on this moment, Alex sees that he didn’t plan enough for fundraising — professionally and personally. 

They were further from product-market fit than they thought, which meant they needed more money to keep going. 

They also hadn’t planned for the amount of data that investors required of them, which led to doing things on the fly. 

To address the personal requirements, Alex recalls that he was still taking care of himself at his time but it wasn’t enough. 

Because of the level of stress he was under, he would frequently fall to his vices as a coping mechanism. 

To prepare for fundraising — Alex compares the physical and mental preparation to a marathon. Paying extra attention to sleep quality, eating well, cutting down on social events to preserve energy, and cutting down on alcohol could have helped him to stay on top of his game. 

Telling people “I’m afraid I’m fundraising” as a means of creating healthy boundaries… which is both amusing and incredibly appropriate. 

He shares

  • Important signs that indicate you’re dealing with burnout
  • How he used vices as a coping mechanism, and what he does now
  • A rough 12-week plan that would have been a more healthy option

In this episode, Alex is very honest about how he handled a difficult situation, and offers lots of practical advice in this episode, for new and seasoned founders.