John Callahan

John Callahan – Chief Marketing Officer at XPENS.ai

Driven by a curiosity for data, John Callahan wants to use his experiences to help grow other businesses.

What’s your story?

I have 25+ years experience in technology in executive GTM, Sales, Marketing operational roles and in that journey have performed as Operating Executives for several PE and, now, VC funds. I have also done several consulting engagements with PE firms looking to make investments in the space I specialize in. Of late, I have taken Fractional CMO/CRO roles and Growth Advisor roles to early stage start-ups and scale-ups. I think my journey has offered me experiences that will have value to Boards and wanted to join Veblum to help me with the processes to attain paid Board engagements.

What excites you most about your industry?

Living near Silicon Valley and having access to all the innovation that occurs (along with the vibrant funding machine that is Sand Hill Road), it is exciting to be part of that ecosystem. As such, the space that I specialize in is not as high tech as the leading edge tech currently coming out of SV. But building and growing companies is something I get excited about. Of course, the successful exits are nice as well. But I enjoy working with a C-team and a Board to put a plan together and then execute it.

John Callahan & family

What drives you in your career to push beyond what other people consider normal?

A blend of Intellectual Curiosity and Emotional Intelligence. Also, there is a certain degree of pressure and danger in growing technology companies that are born and grow in such dynamic environments. I love to find interesting ventures, put a plan together to get some asymmetrical growth or success and then go all in to achieve the goals of that plan.

What have been the most useful skills you have learnt and applied in your journey?

I am always looking at data and ways to get more data. I work well with data driven business strategies and decisions. The more the data and the faster the feedback loops, the happier I am to support, sometimes, complex business strategies and decisions.

What’s the best piece of advice you ever received?

Learn Something New EveryDay.

Learning is essential for personal and business growth.

The Best Investment you can make is in yourself.

Who inspires you?

Richard Branson – his ability to balance business success with social responsibility

Elon Musk – his ability to tackle deep tech projects and convince large groups of leaders and investors to go on the very long journey with him.

Steve Jobs – his ability to capture markets was unparalleled.

What have you learnt recently that blew you away?

That the State of California currently produces the same amount of energy it consumes from renewable (solar, wind, hydro, wave….). Now, not all energy currently consumed utilizes renewable energy (much is still fossil) but the point is the possibility to someday run the 7th largest economy in the world in renewables. Pretty cool.

If you had your time again, what would you do differently?

It would be easy to identify mistakes in life and say “I would do that differently”. But, mistakes are a strong form of learning. Mistakes are not all bad and help personal and professional growth.

But I have taken a much greater interest in the inner working of the early venture world I am now working in and would have liked to have begun that journey earlier in my career.

How do you unwind?

We have twin Golden Retrievers that consume a lot of our time and focus keeping them excercised and that includes lots of walking, hiking and they enjoy our boat, as well. The dogs are our kids so we spend a lot of time unwinding with them.

What is a major mindset change, belief shift or ‘ah ha’ moment that you’ve experienced in relation to your career?

I took a gamble to take a multi-year sabbatical, arguably, at a pinnacle of my career. Walked away from it all and shut it all down. A stressful decision but, in the bigger picture and with perfect hindsight, a very good decision. Good for physical health, mental health and relationship health. There are no guarantees in life and giving it all away there was no certainty I could pick it up again. I am picking it up again with physical strength, mental clarity and strong focus on the 2nd act of my career.

Everyone in business should read this book:

Switch – Dan & Chip Heath

XPENSai Logo on White

Shameless plug for your business or career:

I have had good successes working with leadership teams in later stage organizations growing (organically and via aggressive M&A strategies) numerous businesses to successful exits of

a) public companies sold to public companies,

b) public companies taken private,

c) private to private transactions and

d) IPO.

How can people connect with you?

LinkedIn is a great platform for connecting.

Social Media Links?

linkedin.com/in/johnmcallahan

This interview is part of the CallumConnects series.

About The EnterpriseZone Writing Team

Shining A Light on the Small Business World and highlighting Entrepreneurial Investing Opportunities.

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