By Eleanor Bennett

Interview

5 min read

For the third interview in our series speaking to technology and IT leaders around the world, we’ve welcomed experienced CTO Charles Edge of Bootstrappers.mn to share his journey on becoming a CTO twice over as well as his work as an author of twenty books and host to three podcasts, The MacAdmins Podcast, Jamf After Dark & The History of Computing.

Tell us about the business you represent, how did the idea come about to found your enterprise?

Bootstrappers.mn is an investment firm that helps to fund Midwest and Apple-focused startups as they ease out of the bootstrapping phase of their development. We’re really just founders who have had exits and want to help other founders.

What notable IT challenges have you overcome?

Keeping up with technology over the years (or generations now) has been the hardest part of being a CTO.

Even though I have no technical responsibilities any longer, I still post apps to my GitHub or build little prototypes so I can better understand the challenges the teams I work with face.

That also helps me see through the conflicts that arise between new feature development and technical debt in pretty much every environment I have seen.

How has your business adapted during the Covid-19 pandemic?

We went all remote early on. We are privileged to be in a cloud-first situation and able to go home without missing a beat. We are 100% vaccinated now so looking forward to returning to the office soon!

Being the CTO, what does your day to day responsibilities look like?

I work with a lot of founders. Sometimes that means listening to pitches for investment opportunities and sometimes it means digging into issues within organizations we’ve already invested in more deeply.

Going from speaking at hacking conferences like Defcon and Blackhat earlier in my career - I can say that finding companies that match our investment thesis and helping organizations grow is similar. Hacking business is awesome.

What advice would you give aspiring CTOs and entrepreneurs?

We’ve put building companies on the same type of assembly line that we put education, healthcare, and practically every other industry on in the post World War II boom. People (and companies) can get lost in any of those if we aren’t careful. As much as we have to take control of our own healthcare outcomes when we can, we also have to understand the systems at work.

Angels, round through whatever round to IPO to private equity. There are so many outcomes to understand and just as we pivot products we have to pivot how we think about our own terminal value when it comes to our companies.

That comes with understanding the systems and financial instruments - but maybe choosing when and how we diverge from the norm. The more deliberate we are, the more control we have over our own outcomes.

What new challenges are CTOs facing today?

Budget control. We need to secure devices without running so many agents that a user can’t actually get their job done and in a way that doesn’t consume our entire budget.

Every specialization in the organization wants a "seat at the table” and budget for a hot new SaaS tool that makes them more productive and/or gives more telemetry into their discipline.

Each of those tools has to be considered a threat until it isn’t. Staying on top of protecting the digital assets of the organization while also keeping the productivity gains each person needs is really all about building a culture of innovation.

Because as organizations grow, innovation is bottom-up. It’s the thousands of little processes and iterating towards better outcomes, not some top-down management initiative for “digital transformation” or whatever the latest buzzword is.

We each need a rubric that makes all leaders feel heard and important, even when the tools they want don’t meet our requirements. We have to do so in a way that makes sure our budgets are being spent on productivity gains for every team - and we need to do so transparently and equitably.

Oh and if all that seems easy, we can add one more challenge on top: it sure would be great if people actually enjoyed their tech as well. That’s the sweet spot.

What do you see as the hottest trends within your industry today?

The emerging subfields of security products. We had some larger, disturbing attacks this year that gained a national spotlight.

But every device in every home with all the other devices in those homes trying to move laterally onto it. That’s tough.

We have to protect devices no matter where they are and provide a great experience and consistent productivity gains organization-wide. So aside from early-stage tech that hasn’t really crossed the chasm, tooling that provides added telemetry and protection on devices and gates access to all of our assets based on those triggers is likely to be a substantial buying tornado in the coming months. As will down-market alternatives to enterprise solutions that do those things.

Tell us about your podcasts, what do you typically cover and where can we listen to you?

Oh, I am on three. The first is The MacAdmins Podcast, which is with a really talented group of people in the Apple admin space. A unique attribute about the Apple platforms is the deep knowledge most admins have of the full ecosystem.

The second is the Jamf After Dark podcast. That’s a corporate podcast that showcases things being done at Jamf.

The third is a pet project called The History of Computing Podcast. I’m surprised so many people have joined me on that one. But it came out of working with so many startups that had no idea that, for example, there was a whole era in computing called Time Sharing in the 1970s that is… well… now called cloud technology (ish).

Having authored a lot of books previously, which ones were your favourites to write? Where can readers keep up to date with your latest releases?

The most challenging was one I did on how to start a consulting firm. That came out of a need for closure after being a partner in a firm for a decade. So after I moved into the software world I started working on that book.

All of the books before it were really technical, ranging from network architecture to servers to client management and scripting. But the next two books are on building healthy companies and the history of computers. So I’ll have to get back to the technical stuff to keep my street cred!

As for where to find them - I keep a personal site at www.krypted.com and my Amazon Author Central page is at https://www.amazon.com/~/e/B001JPC32I.

If you enjoyed this article then why not check out our previous guide on everything you need to know about deployment tools?

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