On consulting with Jamon Holmgren

I won’t post the whole transcript here, but I’ll share some key insights and takeaways from my conversation with Jamon.

Work/life balance is hard when building your own business

Not an unobvious one, but Jamon’s time with his family has been hurt by his work in the initial stages of his business. It’s why he almost decided to shut it down, pre infinite.red.

What fixed it for him was partnering up. I, for one, am tremendously afraid of the idea of having a business partner.

You give up so much control and lose so much power in doing so. But if you choose someone that you have good chemistry with. And if you slowly transition into it rather than jumping head first, like Jamon and Todd did. It might just work out for you.

And it seems to be what really unlocked Jamon’s ability to spend more time with his family, fix that work/life balance, and still be able to grow the business and work on things he enjoys.

Marketing, then sales, then everything else

Without a pipeline of work coming in, nothing happens. You can’t pay people well, you can’t pay yourself well. You can’t negociate prices you want or work you like. And you have to deal with the feast and famine cycle all the time.

Without a strong pipeline, as Jamon says, you have an idea, not a business.

Now, there are ways you can “trick” it. Starting out your pre-existent network can help. You can go into a very small niche to make yourself “pop”, so to say.

But ultimately it comes down to the basics done well. Do you have a website that pitches what you sell? Are you taking care of the top of the funnel so you do get inbound?

Open-source work, conference talks, content. These are the things that will get people thinking of you when they need your service. And that’s when they call you. That’s when you can do your “sales magic”.

I’ve seen this so much in my experience as a freelancer and as a contractor myself. When I cold introduce myself, it’s just a lot less likely to get a “yes”. When I have any sort of a warm-up, things are easier. And when the person comes to you by their own volition, it’s the best.

There is no escaping this. Which is what I guess I’ve been personally looking for: a shortcut to making cold outreach work really well so I can make good money TODAY. That shortcut doesn’t seem to exist. You have to be in it for the long game.

Agency vs solo

We didn’t have the time to dive into this as deep as I would’ve liked, but nonetheless I think I picked up a few pointers from Jamon here.

He said in between the two he’d still pick building an agency vs going solo. Partly because he swallowed the tough pill of “I’m actually able to have higher leverage as a business owner than as an individual developer.

But also partly because of an interesting point he made: most developers do not and cannot make it into their old age as ICs. Why? Because the excitment about new ways of skinning the cat wanes as you get older and more experienced.

As much as I’d like to believe that I can do it, and Jamon did say he has employees that are doing it well, I too have seen experienced engineers slowly get bored with engineering.

I guess, even as you transition from paradigm to paradigm and keep yourself on your toes, at some point it all feels very similar.

Watch the video

You should watch the full interview. It was a good one.