I Thought It Was the Worst Day of My Life

Episode 269: I Thought It Was the Worst Day of My Life

Introduction:

This week, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about. That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications. The technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.

— Loren Feldman

Guests:

Ted Wolf is CEO of Guidewise.

Jennifer Kerhin is CEO of SB Expos and Events.

Producer:

Jess Thoubboron is founder of Blank Word.

Full Episode Transcript:

Loren Feldman:
Welcome Jennifer and our newest regular, Ted Wolf. Thanks for agreeing to join us here, Ted.

Ted Wolf:
Thank you very much. I look forward to the conversation.

Loren Feldman:
So, Ted, I did a one-on-one podcast with you a few weeks ago, where you talked about your background and you gave something of a primer for business owners figuring out how to get started using AI. I don’t want to repeat that, but for those who didn’t hear it, maybe just give us a little bit of your background. Tell us about the IT staffing business that you built.

Ted Wolf:
Okay, way back, I graduated from college decades ago, worked for IBM Corporation, and along with my brother, we decided we wanted our own business. So we started a technical consulting and staffing business. It was a total of a thousand dollars we put in, and a lot of sweat equity, and we built it up.

And I would say the biggest mistakes we made were all people-related, because we didn’t know how to hire. We didn’t know how to fire people. We didn’t know how to manage people, in many respects. So I think I had something in common with a lot of people, and that is, I’m not sure about this people equation in the business. Technology? One plus one usually equals two. But with people, it’s a little bit more variable. And I had a lot of lessons to learn in that.

Loren Feldman:
Well, you must have figured something out, because the business got pretty big.

Ted Wolf:
Yeah, we figured out through—actually, I’ll shorten this story. We went into the office one Friday, and we found out that 40 percent of our revenue disappeared overnight by way of accounts. We had an individual who worked for us, who had a non-compete signed. We brought him in, relocated him, a technical manager. He decided he wanted his own business, and took several of our prime accounts and some of our prime people.

So that was an eye-opening event of, “We better change some things,” and we did. And it was all people-related, and that’s an interesting story. But when we changed it, I would tell you that probably five years to the date, almost, we were on the Inc 500 as one of the 500 privately-owned, fastest growing businesses in the United States. And it was all because of the people.

Loren Feldman:
What did you change? How did you solve that problem?

Ted Wolf:
We changed our whole idea about the business. Our initial paradigm, I’ll say, is that we looked at it as our business, and they were coming in to help us grow. And we paid them well and everything, but that small shift had to be changed. And we said: We’re building a company together, and they have to succeed before we succeed. And how do we restructure the framework from silos to more of a team orientation? Get rid of politics. Get focused on the right things.

And it worked out. I mean, it really did. We got great relationships, and we sold it many years ago, and I still get phone calls from people asking what I’m doing. Am I starting another business? And they’d love to work with me again, and that’s gratifying.

Jennifer Kerhin:
Ted, all right, hold on, wait, wait, wait. You grew that fast, and it’s just people. So no process, no new product, new service, new marketing, whatever, just people? Because I’m hiring more leaders right now. Did you hire people with experience from bigger companies? People who were ambitious? People culture? Was it experience versus culture versus ambition? What were the traits that got you leaders to help you grow this fast?

Ted Wolf:
Initially, we hired for skill and brought people in, because it was a technology background. You had the skill. We’ll get you acclimated. But we found that we had to reverse it. We had to hire for culture and then upgrade skills. When we upgraded the skill-set, we basically kept people on the bench who weren’t billing for a pretty long time. We used that as a retraining opportunity, and that attracted other people.

But what we focused on, honestly, was bringing people in who we thought we could build. We could develop their talents. We could develop their emotional intelligence, we’ll call it today. And that was a big change that we made, and we demonstrated it day in and day out. We lived it. And that’s what made the big difference for us.

Jennifer Kerhin:
Who trained them?

Ted Wolf:
My brother and I started training them. We built a whole new onboarding system, and it was all on the values. And the secret to the whole thing was basically having good core values and how to implement them in a business. If you don’t have core values defined, and you don’t know how to implement them, all you’re doing is manufacturing bigger levels of chaos.

Jennifer Kerhin:
People cost money. And when you’re starting off, it’s very hard to afford the quality of people to grow. How did you do that?

Ted Wolf:
Well, we had lines of credit with the bank, because the first 30 days we had to fund the startup till the invoicing came in. And you know, when that infamous Friday came along, which I thought was the worst day of my life and ended up being the best day of my business life, that Monday, I knew I had to go in and renegotiate covenants and lines of credit, and it was embarrassing to say the least. But it was a lesson that I needed to learn

Loren Feldman:
Ted, when you rethought things to try to give your people a sense that they were part of the enterprise, did you focus primarily on bringing them into the conversation about how the company was managed? Or was it about giving them a stake in the outcome—some compensation that made them feel more part of the enterprise?

Ted Wolf:
Well, the first thing that we did is we brought them in on all decisions. So we said, “Here’s what we’re thinking of doing. Here’s what we’d like to do. We have to have your buy-in in order to implement this. So tell us the pros and cons.” And we actually entered into a deep dialog about: What are their needs and desires and where do they want to be? And we knew how to place that in relation to what we wanted to do. We couldn’t come in and just build systems and expect people to change their behavior, because behavior starts with the individual at a deeper level.

So we had to hit that. We had to make sure that we were listening to them, that they knew it. And then we started reframing new systems, and actually we got rid of all titles. We got rid of all personal offices. We put people into teams, and they elected a team leader, and teams were about 10-15 people. They all had an objective to accomplish. And then we instituted profit sharing. We didn’t do what we’ll call today, like equity sharing and things like that. But they all got a piece of the equity when we did sell the business.

Loren Feldman:
How big did the business get?

Ted Wolf:
We had some private equity involved, and we eventually grew to, today’s equivalent in billing would be about $100 million in revenue. And that was acquired by Iron Mountain corporation, which opened up a whole other facet of my life then for change.

Jennifer Kerhin:
Congratulations, Ted. That’s pretty impressive. That’s what every entrepreneur listening to this podcast wants to hear.

Ted Wolf:
A gratifying experience, I have to tell you. But what I learned is the number of zeros in your bank account mean nothing compared to the personal relationships that you can build. And I hope everybody can get to that point of saying: This is all about relationships with people. Clients, people, employees, myself, my family—that’s the most important thing at the end of the day.

Loren Feldman:
Did you feel as though your employees ended up in a good situation after the sale?

Ted Wolf:
Oh, absolutely. We made more than a few millionaires. And in those days, we had a receptionist—in that time, I think she was making about $25,000. She got more in stock that we gave her, because she was there through the buyout and everything than she ever made in a year.

Jennifer Kerhin:
Isn’t that wonderful?

Ted Wolf:
Yeah, I’m very proud of the experience that I had. I’m still making mistakes today, but much further ahead because of that Friday experience.

Loren Feldman:
When did you sell the business?

Ted Wolf:
We actually sold the business—I ended my contract in 1998.

Loren Feldman:
What have you been doing?

Ted Wolf:
I started a number of other businesses. I had an online coffee and tea business to learn more about the internet. As soon as we basically got out of the contract, I started up—gee, a number of different businesses. But I’m on my last one right now with my son, and that’s all about AI, and how do you manage people and business so that it’s a balanced approach with AI? Because you have to get into it today.

Loren Feldman:
That’s Guidewise you’re talking about.

Ted Wolf:
Yes, that’s Guidewise.

Loren Feldman:
When did you start that?

Ted Wolf:
We started that about three or four years ago.

Jennifer Kerhin:
Wow, before ChatGPT.

Ted Wolf:
Yeah, actually it was before ChatGPT. And what we actually focused on was just people’s resistance to change. How do you do change management? I call it “change capacity” now. That’s just a term that feels better to me. How do you build the capacity for people to change? Because that’s all we’re going to have in the future of business, and that’s going to be the deciding factor of who wins and loses.

Loren Feldman:
And who’s your typical client?

Ted Wolf:
Right now, we’re going after SMEs. We have some clients that are doing $7 million, but we have another client that is doing way beyond $500 million. And the solution works for all these businesses. We’re kind of industry-agnostic. We’re going after, I’m going to say, senior leaders and what we call the great middle of a company. That’s your middle managers and supervisors. And then we have training that goes to the frontline people.

But what we are trying to do here is get everybody to live at that intersection of business objectives—results that have to happen in the business—balanced with technology, number two, and then people adapting to change, building that change capacity, so the changes actually take place.

Jennifer Kerhin:
Ted, is this more of a consulting company or a training company?

Ted Wolf:
We’re more of a consulting company right now. We have training that we bring in, but the consulting becomes: How do you implement AI into your business objectives? And that’s the big challenge to get the right use cases in return, where people are having their problems, along with not being able to identify the change. But starting out with consulting right now, but we’re going to be moving more and more to a product orientation, because what we’re doing in consulting, we’re going to build into an agent.

Loren Feldman:
What do you have to do when you go into a new client to figure out what their best use cases might be? What kind of questions do you ask? How do you figure that out?

Ted Wolf:
We have a discovery phase, and discovery is to identify their business objectives and to clarify the business objectives. Because a lot of organizations, believe it or not—even organizations that are doing $100 million in revenue, I have found—do not have good strategy. Strategy is more than a SWOT analysis or anything like that. But if they don’t have that one feature, that distinguishing feature, that in the market is their differentiator, it’s hard to develop a good strategy. Therefore your business objectives get in trouble.

So we go in and look and clarify business objectives. That’s the key thing. What does the business need to achieve over the next 12, 24 months? And then we say, “Okay, here’s what AI can help you do, potentially. And here’s how we then start training your people to adapt to the change of AI.” Because AI is not a technical implementation challenge. When you look at AI, you should be looking at it as we’re implementing greater competency within the organization.

And the reason I say that is because an old technology we’re using, whether it’s Word, an ERP system, or whatever it is: input, process; output, formula. You input your data, the system does the processing. It gives you an output, and that’s where it ends. With AI, it gives you the output. But now you can have a conversation with the technology, which we never had before in technology, and now that conversation completely changes the equation.

Jennifer Kerhin:
Do you have a certain AI that you use quite a bit, or are you agnostic across all of them?

Ted Wolf:
We work with Chat, with Gemini, and with Claude. We do all those, but our preferred platform that we think is the best out there is IBM’s platform, Watsonx. It’s not talked about in the popular press as much, simply because it’s not fun and games. It’s built for business. It’s built to be able to take AI into the enterprise or the whole business, regardless of size. And they’ve just crossed their T’s and dotted their I’s very well. So believe it or not, I started my career at IBM. Now I’m back at IBM as an IBM Business Partner, and we’re certified to sell and implement Watsonx, which is their AI solution.

Loren Feldman:
You’ve also told me about the security aspect of that. Why don’t you tell Jennifer about that, because I think she might find it interesting.

Ted Wolf:
Yeah, when you bring in AI, a lot of people look at it, like Chat, and they’re putting their financial statements on it. They’re putting their own strategy on it. And they’re saying, “If other people see it, I don’t care.” And I think that’s pretty short-sighted, to be honest with you. As a business, if you want to scale, you’re going to regret that in the future. So the whole idea of governance, who can access the data very easily, with this new technology of AI, you need governance, you need all kinds of privacy issues put in place.

And AI does not like silos. It hates silos. So it wants data that everybody can access when needed. And in order to do that, you’ve got to get people to change, because they begin asking, “Well, what am I getting paid for at my job?” And that comes down to the governance and how you orchestrate different agents. When I say orchestrate, I mean: How do you set them up so they communicate with each other, but you’re still managing and directing those agents? And IBM has just thought through that whole governance issue tremendously. In fact, they indemnify you if you’re using their platform for IP, copyright, and those things. And that says an awful lot and brings a lot of confidence to me.

Jennifer Kerhin:
Does IBM send you leads?

Ted Wolf:
Well, we’re in a partner program, and we can get leads, but we’re only in this program for about six months right now. And what we’re doing is just driving our own leads. We’re not looking to them as a lead-gen source. We’re looking at them as: Give me the technology so we can actually get companies to implement it and use it correctly and not waste money or time. Because we’re running out of time and money.

Jennifer Kerhin:
So how long did it take you and your staff to learn the Watson AI?

Ted Wolf:
I’m gonna say we got involved probably about eight months ago. And my son, who, after college, he worked for Deloitte in technology for a while, so he understood that big environment that I came out of: big tech companies and things like that. And he really is the one that dug into it. I’m more of the people business building side, and he is the technology side that we’re relying on. And then we’re going to build accordingly. And we’re looking at IBM, and that partner program is supplying us a lot of technical people, where we don’t have to recruit and hire them all ourselves.

Jennifer Kerhin:
Got it. So you’re the face to the client, but they will backfill your technical support.

Ted Wolf:
Yes.

Jennifer Kerhin:
Interesting. I like that partnership. I’m in discussions regarding a partnership with a tech company, and so it’s interesting how they all do it very differently. Is this IBM’s push, then, to build this program where you’re the first of many?

Ted Wolf:
Yeah, I think IBM gets 9 percent of their revenue from partners like us today, and they are saying, in a very short amount of time—I forget the exact time—but the CEO of IBM said that they want that at 30 percent. And I’m going to say that’s within years, because they see the market change, and they know what’s going to happen. They all do. They know what we’re heading into here, and that’s one way they can not have to hire tens of thousands of people.

Loren Feldman:
Jennifer, you’ve told us here that you’re one of those business owners who have done what Ted was talking about, which is using ChatGPT for strategy, putting in information about your business, including financials. Do you have any pause about sharing that with an AI chatbot?

Jennifer Kerhin:
I don’t. My husband hates it, though. He yells at me all the time for putting this information out there.

Ted Wolf:
Listen to him. Listen to your husband. [Laughter]

Jennifer Kerhin:
The issue is, when you’re small, you can’t possibly think that anybody would care whatsoever about you as a company or your financials. And so it’s hard for me to imagine why I couldn’t. Now, if I was much bigger, I might be concerned. And not that I’m disagreeing. I understand his concerns, but it is just fascinating how AI can look at patterns and easily give you answers of things—or maybe not even answers, but pattern recognition—and point you in directions you might not have considered before. And that’s just inescapable, that humans just cannot do that as fast.

Ted Wolf:
And that’s that whole competency thing of what I mentioned. It’s not a technology input into a business, AI. It’s a capacity-building avenue, I guess you would say, that is incredibly powerful. And right now, you think you’re small. You put your financials out there, and you might say, “We don’t care who sees them.” You may care who sees them, because people with AI can be very creative, and if they are in another country, or they’re not a reputable, let’s say, good character, there’s all kinds of back channels they can go to today in deep web that we don’t talk about—the dark web. You don’t want them knowing all that stuff. I just don’t.

Jennifer Kerhin:
Yeah, I mean, I have no doubt that’s coming, and a lot sooner than we think. I saw an incredible video about a robotic hand, and all I kept thinking about is Luke Skywalker and how close I might see that in my lifetime. But it’s hard as a small business—and I’m sure you’re going into all sorts of sizes—it is really hard to figure out how you do it system-wide for AI, not just individually putting in ChatGPT to help you write an email or help you analyze something. And honestly, I’m relying on my software partners. I mean, I use Salesforce, and I had never gone to Dreamforce, and this is the first year I wish I would have gone to Dreamforce to learn how Salesforce is incorporating AI that can help me. Because it’s both too small and too big at the same time—small that my staff’s using it for emails, but too big to figure out how to do this systemically.

Ted Wolf:
Yeah, well, I don’t know if you knew this—I don’t think it’s public yet—but I was talking to an individual just yesterday or the day before, who knows Salesforce pretty well, and some people there. And they’re officially changing their name from Salesforce to Agentforce. That says a lot.

Jennifer Kerhin:
Interesting. And I saw all the pictures and comments about Dreamforce, and it really did feel like this year they were pushing it hard. And I put it on my schedule to go next year, which I’ve never gone, because of that. Because Salesforce is pretty ingrained in my business, and it looked interesting.

Ted Wolf:
So Salesforce, my daughter works for Salesforce in Manhattan. She’s doing very well with them. She was chosen to go to Dreamforce this year, and she showed us what they’re using day-to-day in customer service inquiries coming in, as far as an agent. I think this is mind-blowing. Salesforce started building customer services agents. They had 9,000 people working in Salesforce for customer service. They’re down to 5,000. They let 4,000 of them go. It’s all agents doing it, and their customer satisfaction metrics have not gone down at all.

Jennifer Kerhin:
Well, it’s probably pretty poor to begin with. I can’t tell you how many Salesforce account managers I’ve had in the last six years, probably 60. They need to do a lot better job on that, to be honest.

Ted Wolf:
Well, they do have an awful lot of turnover. But every company is doing it today because they’re saying, “We don’t have to carry C players anymore.” I hate using the term “C players,” but the average status quo person. They don’t have to, so they’re going to turn them, and the only way they know to do it is: We gotta do it through the churn. They’re going to implement the technology and everything, but that doesn’t mean we’re going to get rid of people. It just changes how that’s going to work.

But Salesforce, the reason I bring that up is because there’s going to be a Salesforce example like that in every industry. And today, we have a leapfrog opportunity to take a small business and turn it into a medium-sized business in years instead of decades.

Jennifer Kerhin:
But your business, you can help companies that are already on IBM or it doesn’t matter?

Ted Wolf:
No, it doesn’t matter. No, we can go in and help an organization. I mean, this is the consulting part, also, where someone might say, “Hey, I’m just not ready to bring in AI. But I need some help over here on the business objectives side.” So we can come in and do that. We just had a company that called us that we work with. They have an AI product they bring into financial institutions like banks and wealth managers.

And basically what they’re doing is, they called us and they said, “Can you come in on the engagement with us as part of that whole change people, change adoption, change management—so that they actually start using the AI and implement it instead of, ‘Yeah, we got a great product, but nobody’s using it.’” So we work with companies that don’t have AI, or smaller companies. We can get AI in there from IBM pretty inexpensively.

Jennifer Kerhin:
What’s inexpensively? IBM sounds very expensive.

Loren Feldman:
It’s more expensive than ChatGPT or the other options, isn’t it?

Ted Wolf:
It is, but what you get is many, many times more value. You can come in an Essentials program for IBM, and you can get in for $600 a month for up to 10 people.

Jennifer Kerhin:
Oh, all right, so that’s not ridiculous.

Ted Wolf:
Not at all. And what you get will be unbelievable. They have a program called Orchestrate, and Orchestrate is just like what you think of with an orchestra. You build an agent. The last thing you want to do is build agents randomly throughout the business. That’s where you get into security problems, and that’s where you’re just building more chaos down the road, because they’re not built on the same core values of the business, and they’re not built on the same algorithms. So that’s where you get into trouble. But you can bring in AI today at IBM to get started, and that’s a great way to get your feet wet and get some guidance to: How do we implement it? It’s doable.

Loren Feldman:
Can you give us an example of a use case at maybe one of your smaller clients that shows the power of this and where we’re headed?

Ted Wolf:
A use case may be something like HR. So, somebody, very quickly, will bring in an HR thing, and they’ll put their policy manual on AI so everybody can just go there, talk to people, and be able to ask their questions, instead of getting somebody from the HR department.

HR is a big area you can use AI in today. There’s a lot of things: scheduling appointments, how you’re going to verify resumes coming in, and things like that. So that is a big area that we see helping. And another area is, here’s an interesting experiment that we’ve done and tells you a lot. We’ve told people, “Bring in your business emails from different managers and or department leadership. Run them through AI and ask them, ‘How do these emails compare in association with core values?’” You’ll be amazed at the patterns that AI will pick up on emails going back and forth between people. It’s staggering. And sometimes, I’d say, you probably need a bourbon before you do this.

Jennifer Kerhin:
I mean, we have that now, right? So Zoom does an amazing job after having meetings. It’s a meeting summary, and then the AI summary, and then you can ask, “How did that conversation go, based on values, based on the SOP for sales? Zoom has that pretty well. I think we also have Copilot, which I hate. I don’t think Copilot’s been helpful at all. I’ve felt that’s been a waste of money, but I feel like the current infrastructure that’s out there, whatever a company’s using, I feel like those tech companies are going to be forced to put AI in rather than—I don’t know, it’s a big leap for a small company to switch.

If someone said, “Hey, switch out of Salesforce for something else,” that’s a massive leap. And my hope is that the places I’ve chosen—Salesforce, Slack—that they’ll help us understand the use cases for AI better, because they’re just so big. And I’ve seen a lot of companies come and go very quickly. It seems like Death Valley a little bit, how quick these companies are going up and down.

Ted Wolf:
No question. I agree with you, and you’ve got to be very careful. And that’s why we like the IBM Platform. IBM, I hope they’re not going away. I think it’s a good, solid company, and I think they’ve got great technology. Sometimes they don’t market the most effectively, but I think they have a great solution, along with Salesforce and people like that, Oracle and those organizations.

Just to go back to what you mentioned about Zoom Info or Zoom, how it analyzes a conversation, I’m going deeper and further than that. I’m saying, actually get the emails from John or Jane Doe—I’m going to make this up—who is your sales manager. And let’s say you have to produce a product. What are those emails like with the people in production back and forth? AI can go in and look at all the email strings and threads and everything, and they start analyzing: Here’s what we see going on in the conversations. Here’s what we see, as far as alignment with core values of the business. When I say you need a bourbon sometimes, you’d be amazed at what people are saying in emails back and forth inner company. Slack might be a little different. But if you look at the emails, that’s just another experiment that you can use that’s pretty interesting and telling about the organization.

Loren Feldman:
Can you give us an example when somebody is not living up to the core values? How does that show up?

Ted Wolf:
Okay, you’ve got emails going back and forth between—I’m going to give you an example—here’s a pharmacy-related client that we had. When he took a look at the emails, very, very good, adept people at the senior level. They were doing about a billion dollars in revenue. They’re pretty sophisticated, well-taught, a lot of PhDs, etc., etc.

So all of a sudden, you get sales talking with pharmacy, we’ll say, fulfillment, and then they’re talking with overall operations. They are saying, “Well, in the conversation, I said this because I didn’t know what else to say.” And it changed the entire flavor of the organization, but they were selling and talking about things that the company couldn’t fulfill. And that would have never gotten uncovered, because they would have gone to the middle of the organization and said, “Just do it. Here’s what we’ve got to get changed if we’re going to make the sale.” Operations looks at it and says, “We can’t fulfill that. It’s impossible. You’re creating a brand new product for somebody.” “Yeah, well, just do it. We’ve got to get it done. We need this sale.”

And those are some of the battles that you don’t think go on in businesses. And that’s also small businesses. I mean, I know companies that were doing $5, $7 million that I’ve worked with that had those same problems. So, all of a sudden you detect a lot of the conflict that’s going on between departments, and you wonder why they’re not working together. They’ve got silos, and they’re throwing things over the wall back and forth and not really solving the problem or the issue and making the changes they need to move ahead.

Loren Feldman:
How big has your company gotten, Ted?

Ted Wolf:
Revenue-wise, we’re a startup, and we spent three years developing our own platform for change management or building capacity for change into people. So this year, we’ll probably do, maybe $600,000 in revenue. But we have a first quarter right now that could change that significantly coming up for what we’re forecasting and what we see, as far as contracts in place and things like that that we’ll be moving on. So I think we can greatly exceed that.

But we spent three years developing our technology for change management and helping people recognize how I have to become self-aware, emotional intelligence, so that I can self-manage, and then become self-leading and self-reliable, if you will. And then in the last year is when we really started looking at: Okay, how do we get out and market it and pair it up with something like AI? And that’s the IBM avenue and other platforms we’re working with, but IBM’s the predominant one. So we’re a small business, but we’ll grow fast.

Loren Feldman:
Is the partnership with IBM your primary method of marketing? Or are you doing other things as well?

Ted Wolf:
Oh, no, we’re marketing outside IBM. I mentioned another account, or another client, I should say, where they have an AI product they’re taking into banks and wealth managers. We’ve already got two contracts not to do AI, but just to do change capacity, breaking down people’s resistance to change. And we’re going in and just coaching. And we have a whole set format of classes and education we take people through.

Jennifer Kerhin:
Where I’m struggling, and we’re thinking about next year, is the theme for next year is client success through automation, and all the different ways that we can use AI for further automation. And to be honest, it’s hard, because there’s a lot of different systems involved. I mentioned we use Salesforce. We use Slack every day, all day. We use another tech system for actual event management. There’s a lot of different software you use, and how do I—like, I have our business objectives. We also use Airtable. And so we are hiring a consultant to help us try to figure out better ways, faster ways, to do Airtable, but—

Loren Feldman:
What’s Airtable?

Jennifer Kerhin:
Airtable is an open-source database that’s very easy to create any kind of need you have on a database so anybody can pick it up. It’s kind of like, do you remember Microsoft Access and FileMaker? Airtable is just very easy to use, very intuitive, just to create databases, and it links to a lot of different other systems. So we’ve used it to create our own event specs database in Airtable.

But trying to connect them is what I’m looking at next year. How do I connect Salesforce and Teamwork? So we use Teamwork.com for our project management. How do I connect those? How do I connect Slack and Teamwork? How do we use Teamwork Desk? And you know, that’s what I’m more interested in, and I think I’m not quite sure how. I’m just confused on how to do it, to be honest.

Ted Wolf:
What you’re talking about is orchestrating. How do I orchestrate all these different technologies, the technology stack, and get them talking? And I know everybody says, “Hey, do your APLs, and it’s easy,” but man, you’re constantly, constantly maintaining them. And that’s why I like the IBM thing. It’s called Orchestrate. How do I orchestrate all these different agents or technologies that are doing things for us together in a seamless manner, that we’re not constantly just maintaining the links and everything? But I think that’s a normal challenge that you have.

And you know, I had an interesting conversation with a pretty large accounting firm yesterday, that has a big professional service practice, in technology and everything. And they said, “Well, we don’t know if we’re going to have to be able to move into it, because everything that we’re using—whether it’s HubSpot and CRM—they’re all putting AI onto it. So we’ll just use that AI, and that’s how we’ll implement it.” And I said, “That’s a great idea, but you’re just going to be status quo like everybody else, because everybody else is going to be implementing it. So how are you going to leapfrog them? How are you going to leapfrog them in competition?” I’d keep that in the back of your mind, Jennifer, when you’re going through what you’re doing.

Jennifer Kerhin:
Yeah, that’s a very good point. You might have inspired me to go take a look at Orchestrate. I will say, the IBM brand, though, as a small business, I think that they would laugh for a company my size. So that’s why it’s interesting to hear you, because I think, “Oh my gosh. Well, IBM only deals with $100 million and above. Why would they worry about a small company like mine?”

Ted Wolf:
Yeah, that’s where their growth is going to come from. In fact, their main target for growth in the future is the SME market.

Jennifer Kerhin:
Interesting.

Ted Wolf:
Totally. They have a whole program, and people set aside just to dig into it, because that’s where that’s where the future growth is going to come from. Because they know we got this leapfrog moment that we’re living in in the next couple of years, and then that window shuts where people are going to experience dramatic growth.

And you know, one thing about AI, just to keep it in the back of your mind, if you start using it, we’re all used to signing a license agreement and paying the licensing fee, and use it as much as we want. But with AI, you sign a license agreement, but then you have usage fees that go with it.

Loren Feldman:
It’s a token system, right?

Ted Wolf:
Exactly. It’s the tokens.

Loren Feldman:
Explain how that works.

Ted Wolf:
Well, to keep it in plain language, it calculates weights, and it calculates how many characters you’re going to be using, etc, and they put that into a weight, and you get so many tokens for X amount of dollars. And when you exceed that, you just start adding on more tokens. And they do it automatically, but you’ve got to really manage it, and that is different than old technology. So the usage you really have to look at, and people just can’t frivolously go out and use it.

And that’s a small business change to put in place, though, but you have to calculate it in your budgets. And then, when you maintain an agent, it costs money to maintain it, just like it does to maintain a human being. So in a lot of ways, when you bring in an AI, and you build an agent, that’s like bringing in a new employee and training them and how they need to work in your business. And that’s where core values come in. So there’s a lot there to unpack in AI, but just be aware, Jennifer, when you get it, you will be paying for usage, not just license fees.

Loren Feldman:
Have you seen examples of that exploding in a way that a business isn’t prepared for?

Ted Wolf:
I haven’t seen it. I’m sure it’s there, but I know that people were working on it. It’s never been a problem because we make them very aware of and say, “Here’s the budget. Let’s make sure you’re putting in a use case that you can afford then.”

Loren Feldman:
How do you keep track of how much you’re spending?

Ted Wolf:
There’s a dashboard, in particular with IBM and Orchestrate. In Watsonx, that platform, there’s a dashboard. Every day it comes up. It tells you exactly what—

Loren Feldman:
So if you know to monitor it, it’s easy to monitor.

Ted Wolf:
Oh, yeah. They’d be killed if they didn’t have that. Nobody wants that month-end shock.

Jennifer Kerhin:
It’s fascinating what we’ll see in a year from now and three years from now.

Ted Wolf:
It’s here. It’s not going away. The big question is, people say, “When do I get in it? Do I wait and not be a pioneer?” If you wait, that leapfrog moment is going to go away. You’ve got to get into it in a low-cost, low-risk environment to learn about it. And that’s what we’re specializing in doing, and why we’re going after the SME market and not the bigger guys.

Loren Feldman:
Jennifer, do you feel competitive pressure to get into AI? Or is it just you want to run your business as well as you can?

Jennifer Kerhin:
Yeah, I don’t feel competitive pressure to do it. I compete with a lot of independent planners who are using Excel spreadsheets. I want to do things faster and better, so it’s more self-induced. And then knowing, you just can’t add staff as you grow. When you’re much smaller, that’s your first go-to: “Okay, we got more work. I’m going to add staff.” And we did a couple things right by adding in technology early on, going to Salesforce, going to teamwork.com, and now the next stage is: “Okay. How do I make this faster and better?”

Ted Wolf:
And that’s going to be AI.

Jennifer Kerhin:
Yeah, I don’t doubt that. I absolutely agree. It’s just where and how, right? That’s absolutely a question.

Loren Feldman:
Jennifer, is there any one thing that you’re really dreaming about that you would like to accomplish technology-wise?

Jennifer Kerhin:
Oh, that’s a good question. Well, we get a lot of customer service inquiries, and if I could figure out how to use an agent to help with that—which seems pretty simple in the AI world, but as a small business, it’s hard to figure it out to do customer service inquiries. We’re an agency base, so we have 40 different clients. And managing the customer service for all of those 40 different clients, I would like to do that. I think that’s probably my first one.

And then analyzing some data through Salesforce, that would be a second one. You get confused where to start. And there’s so many people talking about AI, there’s also a lot of snake oil salesmen out there, and that you have to be really cautious of how to proceed on this.

Loren Feldman:
Have you run into them, Jennifer?

Jennifer Kerhin:
No, I see them on LinkedIn. You know, everybody on LinkedIn is an AI specialist and tells you all of this. And then you dive into a little bit more about them, and you’re like, “Oh, forget it.”

Ted Wolf:
Yeah, you’re exactly right. And I think you’re thinking it through: “Okay, here’s my business case where I can actually improve the business. Now, how can I use technology to help me do that?” That’s the right direction to take. It’s a matter of sitting back and saying, “Okay, how do I actually get some metrics and numbers around these things?” Customer service, you got 40 clients. There’s all kinds of things you can do with AI to better manage their expectations, and how you service them, and where you want to grow their business as revenue streams in the future. But you’ve got to be able to get some metrics around it and start tracking: How many inquiries do we have coming in? What’s the main pattern that we’re seeing? Because it may not be the right pattern. But where would you collect the data and put it together? Because that’s what AI needs. It needs good data. If it doesn’t have good data, it doesn’t work. I think you’re on the right path.

Loren Feldman:
Here’s my dream, Ted: I want to take six years’ worth of podcast transcripts and train a chatbot on it and open it up to paying customers who can ask, “What do the 21 Hats podcasters think about this situation or that situation? How should I proceed to solve this problem?” What do you think?

Ted Wolf:
I think it’s a great use case. Absolutely.

Jennifer Kerhin:
I do, too. I like that.

Loren Feldman:
How hard would it be to do? And what will it cost me?

Ted Wolf:
I can’t answer the cost right now, but where I would start out, if I were you, I would probably sit back and I would try to narrow the scope a little bit instead of saying such a big outcome of, “I want them to be able to ask any question they want and be able to get something back.” You’re going to have to be able to prompt and give it more guardrails on how it’s going to determine those searches.

So I’d break it into smaller pieces of what an agent will do, how you’re going to do it, and you work in the small piece, get that working. Then go to the next one, and the next one. In other words, you take the elephant and break it down into bite-sized portions. That’s what I would do. And I think you’ve got a lot of data, between podcasts and blogs and articles on your newsletters and all that stuff you can put together. But you’ve got to, I think, break it down a little bit, not so general, but more specific.

Loren Feldman:
All right, well, that gives me something to think about. Thank you. Thank you both, Jennifer Kerhin and Ted Wolf—Ted especially for joining us for the first time.

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