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Hackers, Hustlers ... and the 3 Things I Would Have Done Differently

Andy Crestodina, Co-Founder and Chief Marketing Officer of Orbit Media Studios which helps companies with web design, development, and strategy, shares a number of valuable marketing tips and insights. 

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Photo Courtesy of Pexels

Guest Author: Andy Crestodina, Co-Founder and Chief Marketing OfficerOrbit Media Studios

I was a startup. It was April, 2001 and I was trying again. This would be my third attempt at launching a business. The first one was a bad idea. The second one had a bad partner. But this time, I was going to do it right.

Keep it simple. No debt, no investors. Just one business partner. I had a few thousands dollars in a old 401k. He had a tiny bit of savings and a credit card. We’d offer a simple service, web design.

Nothing fancy. Just two guys, two computers and a phone.

Like most startups, there were two people and two jobs. We both wore a lot a lot of hats, but it broke down into two classic roles:

  • The Hacker – Resourceful problem solver. Builds the tools or the core service.

  • The Hustler – Empathetic marketer. Promotes the product or service.

Apple, GrubHub, Hewlett Packard and thousands of other startups started with this same structure and these two partners. Just as restaurants have cooks and waiters, startups have hackers and hustlers. One creates the product or service. The other connects it to the world.

I Suck at HTML

I don’t know how to program websites. I don’t really know how to build anything. But I can do a bit of design and I can sell stuff. My partner Barrett was the programmer. He’s amazing. He can build anything. So I was the waiter and he was the cook.

As time went on, we grew a little, hired a bit and started taking off hats. We started hiring and delegating. My role evolved and I eventually stopped designing websites. Then I stopped managing projects. Eventually, I even stopped doing sales.

This little chart shows how my role has evolved since day one. I’m the blue part of the chart.


I still work on certain projects and I still help the sales team when they need it. But I’m focused now on the one area where I can make the biggest difference -- marketing.

I Could Have Done This Faster

Today, we’re a team of 35+ designers, programmers, and project managers with revenue of $5m. Growth is slow, but steady. Web design is a competitive industry and a challenging service to offer, but we like it.

It took 17 years to get here. That’s a very long time. If I did it again, I would do it differently and much much quicker.

Yes, we could have built a platform like WordPress. We could have build a product like EventBrite. But setting aside the big, world-changing missed opportunities. I’m thinking about how I could have built this business faster. How I could have been a better hustler.

Here are the three things I wish I had done years sooner as a marketer:

  • Start the blog earlier.

I wrote my first post in 2007. It wasn’t until 2010 that I realized that writing and publishing was one of my key roles as the hustler. It took me years to figure out the mechanics of content, search optimization and lead generation.

Everyone seems to think that blog readers turn into leads. We’ve all seen this funnel diagram, right?


The truth is that content is a key part of search and lead generation best practices. And if you want to rank for the super valuable keyphrases, you need to have an authoritative website. And that’s only possible with a lot of content.

Had I started sooner, I could have build a position of dominance in a far larger market. It’s a big missed opportunity. But the timing may be good for you so.... start publishing your best advice early.

  • Grow the list earlier.

But writing takes a lot of precious time. There’s high risk that the time will be wasted. That’s where my next regret comes in and my next bit of advice for any startup: optimize your blog’s email signup form.

The percentage of your readers who subscribe has everything to do with the design of that little box. If you make it visually obvious (prominence), tell people what kind of information going to get (promise) and show that your legitimate (proof)’ll get a lot more subscribers.


Source: How to Start a Blog, Orbit Media

After I figured this out, I started growing my audience much faster. We went from a dozen subscribers per month to a dozen or more each day. I attribute most of that success to the design of our email signup box. 

Had I done this sooner, I would have a much larger audience today. But the timing is good for you so ... optimize your email signup box to maximize list growth.

  • Create a mastermind group.

Books, blogs and podcasts. I’d any source of knowledge and got into “sponge mode” as often as possible. I still study like it’s finals week on all kinds of hustler topics using all kinds of formats. But there is one way to learn that beats all the rest: a mastermind group of peers.

There are people out there who already know what you need to learn. They have the answers to your questions. And you may have answers that they need. If you create a structure to talk regularly, you can all help each other directly.

Form a small group of 3-5  people with similar situations. Do a monthly video call or meeting. Come with an open mind and be ready to help. Ask each member these questions:

  • What’s working well for you? I’ve learned…

  • What do you need help with? I need to learn…

  • What blogs, books, experts do you recommend? I discovered…

Miss it twice and you’re kicked out. Or just let it expire after one year, then form another. Or start several, each a different focus. The cost is zero. But it has huge benefits to your knowledge, your network and your morale.

I eventually figured things out, but by not forming more groups earlier, I missed an opportunity to learn faster. But it might still be good timing for you so ... form a mastermind group of peers who can teach each other quickly.

If I Knew Then What I know Now

I would have done things differently, with fewer mistakes and faster growth. But these aren’t serious regrets. Mostly I’m happy to have done what I did. And happy to share what I’ve learned with anyone who will listen. Thanks for reading.


The opinions expressed here by 1871 guest writers are their own, not those of 1871. To learn more about Andy Crestodina or Orbit Media Studios, follow this link.

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