Horizontally or vertically, everyone exits their business. You decide if you want to walk out or be carried out.
Artificial Intelligence is transforming industries at a breakneck pace, and the entrepreneurs driving this innovation are at the forefront of this revolution. From groundbreaking applications to ethical considerations, these visionaries are shaping the future of AI. What does it take to innovate in such a rapidly evolving field, and how are these entrepreneurs using AI to solve real-world problems? As a part of this series, I had the pleasure of interviewing Ian Richardson.
Ian Richardson is the founder of Fox & Crow Group, Inc., the AI software company he built after founding and running his own IT company for sixteen years before its acquisition. Early in his career, he learned that his seven-figure company was “essentially worthless without him running it”, and that lesson drives the decisions around the development of the AI products Fox & Crow Group builds for Managed I.T. Service Providers and the channel vendors who sell to or through them. He spends his spare time “vanlifing” in national parks, and he’s actively preparing his own children for careers in an AI-shaped future.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your childhood backstory and how you grew up?
I grew up in a middle-class household in a wealthy area in Michigan. We weren’t “poor” but by comparison, we were noticeably less “well to do” than the average family.
My father was an entrepreneur: He had his own medical practice.
My mother was a Neo-natal intensive care nurse, who then got sick. With my mother sick and my father absorbed in his practice, there wasn’t much supervision at home. Like plenty of boys in that spot I felt different from the kids in my school and neighborhood. I got into a fair amount of trouble early on. In my early college years, I had a couple of near misses with society and authority figures that helped get me onto the straight & narrow. I started an IT business that became my focal point when I was 21.
Can you share the most interesting story that happened to you since you began your career?
Interesting is such a relative term.
There’s certainly been high stress items in my career: coming from I.T. infrastructure, anytime there is a system outage or data loss event, you’re in a stressful situation. They’re not necessarily interesting.
I went to lunch with a reporter in Philadelphia and met the woman who is now my wife. That was certainly interesting — and unexpected. I wasn’t in the market to find a wife at the time.
Most days in my businesses aren’t interesting at all. That’s by design. I run process-driven organizations. Interesting points towards process failures. Great businesses should be predictable. Boring, even.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
When my business crossed the 7-figure threshold, I qualified to join an I.T. industry peer group. That collective group helped me more than any one person. During my very first meeting I had ten or so minutes to tell my story.
I told the room about my amazing, fast-growing business, expecting my peers to be impressed with all I had achieved.
The other owners in the room said I didn’t have a business at all.
They said I had a fancy, stress-filled job and a company that no one would buy due to lack of enterprise value.
Over the next year I added 50% revenue and grew profit from break even to over 20%. That advice sticks with me now.
All businesses MUST be built for exit, because we must all exit our businesses.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Horizontally or vertically, everyone exits their business. You decide if you want to walk out or be carried out.”
I first heard that quote (or one like it) from Arlin Sorenson, the owner of the industry peer group I joined.
That focus on the eventual exit from a company helped me think differently in two ways:
One, my business must always be built and ready for sale. You can’t take your company with you at the end of your life, and you might not have a lot of time to plan. I experienced first-hand how an unexpected illness impacts an unprepared entrepreneur.
Two, it narrows a business down to what it truly is: a vehicle for wealth generation for my family. My business doesn’t care about my mental health, my physical health, my marriage, or my family. Your business is not your life. Your business funds your life.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
I don’t get distracted. I create a plan; I work the plan and the plan works. We had a client whose 20+ years of legacy CRM usage without data policies had created a database that would have taken them six months and over 50,000 in payroll and professional services to clean up and migrate. Adding more sales resources was an immediate priority, but it would have scaled both the cost and complexity of the essential migration. After understanding the issues, I was able to build them a CRM that solved their problem for less than their migration budget — in under a week.
I have an ability to focus on the big picture combined with an analytical mind. Before starting Fox & Crow Group, I was hired to prepare an I.T. focused call center for exit. I realized the data generated by the call center was far more valuable than the contracts or brand and convinced the owner to complete an asset transaction and maintain the data even though it lowered their value at the time. The data was used to form a much more valuable AI business post-transaction.
I’m a task-focused extrovert. That one is a double-edged sword. I don’t have a lot of deep relationships outside of my family and close friends because I’m focused on the tasks, versus the people. I’ve lost clients because I was unable to empathize with their inability to set aside emotions in business. I simply do what’s next on my list. How I’m feeling that day doesn’t impact my calendar. If it needs to get done, I do it.
That lack of relationships is something I am actively trying to focus on; I’d consider myself fair at best in terms of success.
Ok super. Let’s now shift to the main part of our discussion. Share the story of what inspired you to start working with AI. Was there a particular problem or opportunity that motivated you?
When my wife and I sold our existing businesses, we both consulted for a couple of years in the Managed IT industry. One theme kept coming up: people needed help with New Logo sales. Carrie had operated an outbound call center that scheduled qualified sales appointments for managed IT firms and specialized in reseller partner recruitment for the software and hardware manufacturers that sold through those firms. We took the data she had, plus my industry experience running one of those companies for 16 years and built a pair of tools. The first was a large data platform for IT channel vendors, helping them target Managed Services Providers (MSPs) more efficiently. Helping a vendor trim 12 months off their go-to-market efforts is significant value. We took what Carrie had done manually with her team and automated and extended it with AI, finding, classifying, and enriching a dataset of 100,000 companies worldwide with a team of three. I would never have thought that possible. The second was for the MSPs themselves. We had 10 years of calling data from the call center, plus a decade of hard-learned sales lessons from doing the “wrong thing” enough times to learn what worked. We made those lessons transferable and trainable, then built a full software suite around them. An MSP can use it to get new customers faster and more predictably than ever. AI is at the core of it: it tracks everything the MSP does and coaches them as they go, delivering consistent week-over-week 1% improvement across the board. That kind of methodical sales improvement leads to real magic when it comes to growth.
Can you describe a moment when AI achieved something you once thought impossible. What was the breakthrough, and how did it impact your approach going forward?
These days that happens almost weekly here!
Two really stand out.
We took a 2000 call sample from the call center.
Every call had a “successful appointment” booked out from it.
We hand judged each call on a 20 metric scale.
AI was able to take that hand-assessed value and “learn” how to judge a cold sales call.
We now have custom-trained software we use with our sales reps to help them improve their outbound calling skills.
It processes thousands of calls every day and can deliver custom guidance on each of them. It’s wild that we have been able to build that. It was what steered us to continue to invest in servicing our customers in this way: I believe we’ll eliminate most expensive coaching services through this software for our customers (and any other MSP in the industry) within the next 24 months.
With our data platform, teaching the software how to do an online audit of a business in any English-speaking market and identify it as a potential MSP, then review and score the business, and add them into the dataset without ever having been in that market itself is something I didn’t think possible.
Now we’re taking those data streams and using them to find additional data sources, then inject them, and classify them in a way that I find interesting.
Our customers receive deep intrinsic value from this. The platform replaces many labor-intensive tasks that were essential to the success of enterprise sales organizations: data entry, database hygiene, and quality control. And they’re not just entry level tasks. The platform reduces managerial or executive tasks that were repetitive, boring, time consuming and incredibly prone to human error or objective decision making. The market reception has reinforced that what we’re doing matters a great deal, and we will continue to evolve the platform.
Please talk about a challenge you faced when working with AI. How did you overcome it, and what was the outcome?
Everyone has heard that “AI hallucinates.”
Running products that are entirely dependent on accurate data makes this challenge a business-survival level of criticality for Fox & Crow Group.
Discovering the concept of being able to program AI to require itself to use sources for data analysis, and disallowing it to generate responses has been a game changer for us.
Can you share an example of how your work with AI has had a meaningful impact (on others, on business results, etc)? What was the situation, and what difference did it make?
We’ve had multiple MSP clients that were “stuck” at a revenue figure before we started working with them report massive success.
One of our clients is even at the point where the owner is functionally retiring after working with us for 18 months.
This was the “last challenge” he had to deal with before stepping down. Not being able to grow in a predictable way is a huge business risk, and we’re able to reliably solve that for our MSP clients.
For channel vendors, our customers have reported that we’ve solved problems that have accelerated their GTM (go to market) motions by 12 months or more.
With no defined NAICS or SIC industry classification codes for an MSP business, there are hundreds of thousands of companies in the US alone that “look like” or “might be” an MSP IT firm. Of those companies, more than 70% are SOHO or “hobby/lifestyle” IT businesses that aren’t ideal targets for any channel vendor. Our platform stops the guess work.
One client estimates we’ve eliminated five FTEs worth of payroll they needed just to determine “is this company an MSP or not?”
Here is the main question for our discussion. Based on your experience and success, can you please share “Five Things You Need To Know To Help Shape The Future of AI”? (Please share a story or an example, for each.)
- You’re not late — you are early. AI adoption is still very nascent. Make a plan, assess your products and workflows, and find out how you can strategically invest in AI to deliver the best ROI for your business. While a lot of people are talking about AI on social media in our industry (IT outsourcing), less than 2% of MSP businesses are advertising structured AI offerings in any meaningful way.
2. AI can be tuned to be data-driven. Use of pydantic-AI and other tools can help. Taking time to properly understand the capabilities of AI is time well invested. Don’t try to do this in a vacuum — there are plenty of specialists who can assist you in this effort. We utilized the services of data scientists and AI experts to fill in our knowledge gaps in early days. Paying experts in the beginning may save you from expensive rework in the future.
3. When you build a robust AI application, chances are you will be able to reuse some or all of the AI you have built for other purposes. When we started this journey, we had one application. We now have 6. We have taken items we have built and reused 80% of them for other business outcomes. This has shortened all sorts of development cycles. It also opens the ability to increase revenue from your efforts.
4. Remember that at the end of the day, your users of AI are humans. AI is not the bogeyman. There will always be humans involved in work because we interact with and buy from each other. A computer cannot replace a person; it can only augment what that person does. We don’t let AI do our accounting — we aren’t accountants. Our accounting firm probably uses AI and that’s fine, they are the subject matter experts with the oversight needed.
5. Don’t worry so much about models. AI is like any other project: the more you know around use of the product, and the better your project plan, the better your outcomes will be. AI models changing is like an employee resigning — you should have a succession plan in place and documentation to allow for an immediate transition in the case of an unexpected issue.
When you think about the future of AI, what excites you the most, and how do you see your work contributing to that future?
AI is equivalent to the type-writer, and the personal computer.
It’s changing the face of work.
Being able to be here while this launches, grows and changes rapidly is intriguing and exhausting all at once.
My biggest focus on is on my children and making sure THEY are well equipped for their careers. I can just retire if I get tired, but they’ll need this moving forward.
What advice would you give to other entrepreneurs who want to innovate in AI? Can you share a story from your experience that illustrates your advice?
Start learning today. If you truly want to innovate, you need to understand the underlying technologies.
You cannot just “vibe code” yourself into success.
Learn the basics of programming and infrastructure design or hire those roles out.
Building with a solid foundation prevents rework and issues later one. The background I have from 20 years in industry has served me well when it comes to knowing what must be done to create scalable, secure applications for customer use. My partner had no I.T. background. When we launched the business, she enrolled in Vanderbilt University’s online AI program. She doesn’t build our products, but it was still essential that she understand them.
Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. 🙂
I’d value the opportunity to sit down with Senator Slotkin. She’s the person making the most sense in my state currently.
How can our readers further follow your work online?
You can find me on Linkedin at https://linkedin.com/in/ianalexanderrichardson
or check out what we’re building at Fox & Crow Group, Inc:
https://foxcrowgroup.com
https://facinstinct.com
https://facjackdaw.com
Thank you so much for joining us. This was very inspirational, and we wish you continued success in your important work.
About The Interviewer: Gabriel Borden is an American investor, advisor, and entrepreneur. He is the managing partner of Arrow Fund, a private investment firm with publicly reported assets under management of about $150 million. In that role, he has overseen investments spanning technology companies, private markets, media, and special-situations opportunities. Borden attended Loyola Marymount University from 2012 to 2016, where he studied business. At Arrow Fund, Borden leads a firm focused on technology, private markets, and event-driven opportunities. The fund has invested in a number of private companies tied to innovation and growth sectors. Publicly reported investments have included Polymarket, the prediction market platform; SpaceX, the aerospace company founded by Elon Musk; and Valar Atomics, among other private technology businesses. The firm has also expanded beyond minority investments into direct ownership of operating companies. In a recent transaction, Arrow Fund acquired a majority interest in LeVecke, a California-based bottling and beverage manufacturing company. LeVecke has been reported to generate roughly $220 million in annual revenue and operates across beverage production, bottling, and distribution. The deal signaled a broader strategy that combines financial investing with hands-on ownership in established industrial businesses. Before launching Arrow Fund, Borden held senior roles managing capital for prominent entrepreneurs and private investors. He previously served as managing director of the family office of Brock Pierce, where he worked on investment management and portfolio strategy across technology, media, and real assets. Family offices, which manage wealth for individuals or families, often invest with longer time horizons than traditional funds and can move across industries with greater flexibility. In that setting, Borden’s responsibilities included evaluating opportunities and overseeing portfolio decisions in multiple sectors. Borden comes from a family involved in creative and design fields. He is the son of filmmaker Bill Borden, a producer known for commercially successful films including the High School Musical series, La Bamba, Desperado, and Kung Fu Hustle. His mother, Melinda Gray, is an architect and the founder of Gray Matter Architecture, a firm focused on modern design. That background placed him in an environment shaped by both entertainment and entrepreneurship, industries that often rely on risk-taking, financing, and long-term project development. While Borden’s own career has centered on investing rather than film or architecture, those influences connect his professional path to a broader family history of business and creative work. He is married to Sydney Borden, and the couple live in Santa Monica, California. As private markets continue to attract more capital and expand their reach into sectors once dominated by public companies or strategic buyers, investors like Borden represent a model of finance that blends traditional portfolio management with direct ownership and operational involvement.
Ian Richardson of Fox & Crow Group On Pushing the Boundaries of AI was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.