Mastering the Art of Failing
Mastering the Art of Failing Podcast
Mastering Failing: Crashed and Burned Into Customer-Market Fit

Mastering Failing: Crashed and Burned Into Customer-Market Fit

Season One, Episode One: To kick off our pilot, we chat with Glen Hellman, who discusses finding customer-market fit… and losing $100K.

Find us on Spotify, Apple, YouTube, and Audible.

In another life, he was known as Mr. Cranky, a prolific entrepreneurial voice in the Washington DC area who ran on the platform of authenticity, honesty, and organizational growth. As an investor, he saw successful exists and flops; as a business leader, he grew companies and optimized them.

Today, Glen Hellman has left that brand behind and has shifted his energy toward guiding founders, executives, and other business leaders on their own journey toward success through the University of Maryland and other ventures.

This week we chat with Glen about finding customer-market fit. Think product-market fit, but if it was branded a bit more appropriately. But, before we get inside Glen’s mind, we first learn about the experiences that led him to understand why customer-market fit is so crucial for building a profitable or high-growth business, and why it also took a $100,000 loss to get there.

Producer’s Note

Welcome to the first episode in our pilot season for Mastering the Art of Failing (we’ll typically shorten this to Mastering Failing).

Alex Love and I (Elliot Volkman), in a past life, launched a non-profit, Digital District, dedicated to creating an environment where people of all backgrounds could safely fail, learn, and grow. We had a blast doing it, but it ultimately didn’t pan out the way we wanted (that episode will drop soon). Maybe we never fully scratched that itch or we just love adding a bit of chaos into the world by putting cracks in the rose-colored glasses of life, but either way, we feel this series has the potential to help others navigate failure. So we developed a simple mission that’s tied to a hefty vision of destigmatizing what failure means.

Our mission is to bring failure out into the open so others may learn from it while showing you can still find success.

And that is where Mastering Failing was created.

Over the coming episodes, you’ll hear from people who have invested, built, created, and crafted who they are today. You will also learn about the failures, challenges, and occasional fuck ups that live in the past. As we develop this series, we plan to chat with people from all walks of life, not just from the world of startps, but also athletes, artists, creators, and those deemed successful in the public sphere.

If you enjoy these stories and the people behind them, we hope that you’ll subscribe here and on your favorite podcast platform. If you love what we’re doing, we’d love to hear any feedback (critical or complimentary) that you can email us at

If you have suggestions for future guests, feel free to send a tip to the above address, too.

Thanks again for being here on day one.

Key Takeaways

  • Conduct unbiased customer discovery before launching a product or service, interviewing various stakeholders to understand their needs, pain points, and satisfaction levels.

  • Learn from failures and adapt by constantly reassessing market conditions, technology advancements, and customer feedback.

  • Emphasize critical thinking in coaching entrepreneurs, guiding them through a process of self-discovery and helping them develop their own strategies.

  • Customer discovery is crucial for achieving customer market fit and increasing the chances of success.

  • Prioritize understanding the needs and satisfaction levels of different stakeholders, including end-users, decision-makers, and industry experts.

  • Select a beachhead market with a high priority, low satisfaction level, and potential for early adoption.

The Importance of Customer Discovery

Hellman emphasized the importance of conducting unbiased customer discovery prior to launching a product or service. He highlighted the necessity of interviewing different stakeholders, such as end-users, decision-makers, and industry experts, to comprehend their needs, challenges, and levels of satisfaction. By obtaining insights into the target market, entrepreneurs can align their offerings with customer preferences and enhance their likelihood of success.

Learn from Failure and Adapt

Reflecting on his own failures, Hellman acknowledged that he had made similar mistakes multiple times. However, he highlighted the importance of learning from these failures and adapting one's approach. He emphasized the need to constantly reassess market conditions, technology advancements, and customer feedback to make informed decisions and pivot when necessary. Hellman's experience serves as a reminder that setbacks can be valuable learning opportunities on the path to success.

Critical Thinking and Coaching

As an executive coach, Hellman emphasized the role of critical thinking in coaching entrepreneurs. Rather than providing direct answers or solutions, he guides his clients through a process of critical thinking and self-discovery. By asking thought-provoking questions and challenging assumptions, Hellman helps entrepreneurs develop their own strategies and make informed decisions. This approach empowers individuals to take ownership of their choices and increases their chances of success.

To listen to the full conversation and explore future episodes of Mastering the Art of Failing, visit

Show Transcript

Mastering Failing uses automated tools to create a transcript of our show. Please excuse any typos and hallucinations that we’ve come to love from our new AI overlords.

Glen Hellman: Hey, I'm Glenn Hellman, and I'm going to tell you about my first personal business failure. I was part of a team at Progress Software. We went public, and fortunately, I was there early enough to make enough money. And so then I joined an ex customer of mine, and we started our own company. And I put 100, 000 of my own money into it.

It was a sales automation system before there was Salesforce. It was we got pretty good funding. And we crashed and burned.

Elliot Volkman: Hello, and welcome to the official first episode of mastering the art of failing.

I am Elliot, Volkman the producer and also cohost alongside Alex Love. This is going to be a pilot season. So if you enjoy what you hear, please absolutely let us know so we can determine what direction we're going to go. If any direction. In just a moment, we're going to hand this back over to Glen Hellman, our wonderful first guest, but just for a little bit of context on what we're building right now, this is a series not just devoted to successful leaders, business folks, founders, but people in life who have experienced different pains and areas of vulnerability and have been able to overcome them and use those challenges as a tool to grow and move forward. So, if you like what you hear, provide us some feedback and hopefully we'll stick around.

To learn more about our series and podcast. Just go to failing You can subscribe to our sub stack there. And of course, on your favorite podcast channels. All right, Glenn. It is now off to you.

Glen Hellman: We crashed and burned for two reasons. One is... didn't do enough customer discovery to understand that people who had to make the system work, the sales force, didn't really like the amount of transparency we provided to their bosses.

And so they sabotaged the system. And the second thing was at that time the internet wasn't ubiquitous. In fact, it was non existent in the commercial world outside of universities. So we required dial up, which the technology just couldn't Today, if we did it, the technology side would still work.

Probably the transparency side still wouldn't. So we, I had a hundred thousand dollar loss. The VCs had a 6 million loss. And what I learned is do customer discovery and make sure the technology infrastructure is there before you start something.

Alex Love: Glenn, why don't you tell us a little bit about what you're doing today and how you learned from that failure?

Glen Hellman: Today I have two jobs. Half time, I work for the NSF, National Science Foundation, who pays University of Maryland. And University of Maryland, I teach university researchers from 11 universities that include Carnegie Mellon, UPenn, Maryland UNC. And we teach these people who have incredible inventions, world changing inventions, like turning wood.

Which is a renewable resource into a replacement for steel. That's cheaper than steel, lighter than steel, and just as strong as steel. Or, so things that can actually change, and it's renewable. So things that can actually change the world. I do that half time, and the other half time I'm an executive coach.

I work with people who are starting companies. And I ask them a lot of questions. And I challenge them. And I'm a place where they can go for unfettered. Advice without a agenda.

Alex Love: Awesome. Sounds good. Yeah. And we met a long time ago, at least 10 years ago. Probably in a combination of things. So you definitely came into the digital district world. And I think I helped out with some of the. The nonprofits and projects that you were working on when I was at GW for my MBA. So we've interacted a couple of different times in different focuses.

So it's been cool to see what you've been doing over the

so Let's dig back in to your failure. So you mentioned dial up. So should we make the noise together? No, I'm

Elliot Volkman: I'm adding that That's going right on top.

Alex Love: It's been a minute since I've heard that noise or at least coming out of my computer. So why don't you take us back to, you know, how did you get involved with that initial, you know, startup? What interested you? What was your role? And you know, like, how did you sort of get into that situation in the

Glen Hellman: So Progress, one of my customers company was a manufacturing system. And the CEO of that company went public, left the company, and asked me to join it. So I was going to run the business side, and he was going to run the engineering side. And I ran sales and marketing. Matter of fact, I invested a year before I joined the company because they did their software development.

And there's a big difference between doing a startup today and doing a startup 15 years ago ups. One of those big differences, if you got funded 20 years ago, that was first of all, you didn't have to have revenue because to create a company. required at least three to six million dollars because you didn't have the internet.

You had to hire people who worked in your office. You needed to buy and support multiple computer systems because there were so many different types of computers that you had to operate on multiple. So it cost a lot of money. So if you were one of the five companies who got funded, you were probably going to make money.

For instance, Progress Software. We were probably the third best company in the market out of five. And when we went public, we made, we made it was a 360 million public offering. Number one was Oracle. So you know, it

Elliot Volkman: to compete

Glen Hellman: that was, so we yeah, Progress is still there. They're not the same company.

But it was just getting money from a VC. Almost guaranteed success that you would finish on the, you know, on the, you would be one of the top five finishers. Whereas today, because of open source outsourcing the fact that people don't have to come to your office and that pewter power is portable you know, with c and c plus plus you can run on any platform.

It only takes about $200,000 to start a company and therefore. The barrier to entry is so much lower that there are so many more competitors and because of this VCs have become much more risk averse. They don't invest as early as they would have Because their money doesn't guarantee success.

Elliot Volkman: that, that actually brings up an interesting point. I could be misspeaking here, but obviously beyond what you do today, you, you're, you are an angel investor, or you probably still are, but like, you are,

Glen Hellman: I am not,

Elliot Volkman: no? Okay, I screwed up. heading this out.

Alex Love: lesson.

Glen Hellman: can tell you that too. So angel investing to me was angel philanthropy. Okay. I give my money to it with, with, it was more fun than giving it to the American heart association or the American cancer association, but I assumed I was going to write this off. Now, if I gave it to the American heart association, you'd be able to write it off the day you wrote the check.

It took seven years to write off a lot of my investments in the other, I have one still that's alive and 15 years old. So I did, so I had made a total of 11 investments and I made about 150 percent on my money, 50 percent over. Had I invested in the SAP, the same amount of money, I would have made about 250%.

At one, one thousandth of the risk, lower risk. So I am no more, I am no longer a venture philanthropist. Put my money in a safe place.

Elliot Volkman: little less stressful.

Alex Love: That's fair, yeah, that's

Glen Hellman: Yeah, I've done my part. I've, I've tried to help a few companies and I've added those. I had two successes, which was you know, I was the first investor in social tables.

Don Berger, which pretty much that's where most of my profit came from. And then there was another one that was, and boy, I forgot the name of it, but it, when I, that one paid off everything I invested. So when Don came in, it was all profit.

Elliot Volkman: It's crazy. I mean, you know, at least it worked out for you. I mean, I, I know just as many people who have just burnt themselves out and they will never invest again.

Glen Hellman: You have to do a portfolio approach. You have to, have to do it over time and you have to place a lot of bets if you're going to make money.

Elliot Volkman: Yeah, absolutely. And I don't know, it's kind of wild that you even brought up social tables. I am familiar that you kind of put money in there, but. I even use that myself today. So like the fact that your dollars stretched into something that people are using. Can't remember who bought it.

Might be Cvent

Glen Hellman: With Cvent. with Cvent. It was a hundred million dollar sale, which, know is pretty good. oNe of my, yeah, yeah.

Elliot Volkman: I think that's fantastic. You know, regardless of, like, the breadth of experience that you have, you've been through, like, the seed stuff, you now chat with people, walk them through it. So they know what they're going to be getting into. I'm sure they're having conversations with similar people who have been in those shoes.

So that kind of experience it doesn't come from just, You know, out of the blue, it comes from exactly what you just said you've run into some scenarios, which didn't always pay out some, you know, paid off for the, the mistakes. But obviously you know, you learn through experience in those situations.

Glen Hellman: So, let me so in my coaching job as a coach, the best coaches I've ever met don't have business experience. They're psychologists. Because if you ask me, uh, if you, if, if you ask me what would you do, I would do you a disservice if I said this is what I'd do. My answer would be, I could tell you what I'd do, and it might work if you were me.

We are here to figure out what you would do. So sometimes, pattern recognition gets in the way of helping somebody make a decision. The real value of a business coach is critical thinking. The kind of critical thinking, for instance, that can look at a company like Trustify and say, this is a scam. This is never going to work.

This guy is lying. So it's critical thinking and then forcing your mentee or the client that you're working with, asking the questions, but they need to come up with the answers themselves because people have a higher probability of succeeding in plans they've developed themselves.

Elliot Volkman: Yeah, that absolutely makes sense. And I, I feel like I can add a little bit of color to that scenario. Only a little bit and for the record our first episode, Alex and I were trying to like, figure out what our kickoff is going to be. I was like, that is it. Working there, trying to fix it from the inside, which was not going to work.

Only to find out that the CEO essentially used social engineering to defraud investors. Yeah. I don't know how much critical thinking would have avoided that scenario. Like that was, that was a pretty intense amount of things going on to yeah, get that

Glen Hellman: So if you were,

Alex Love: the situations I'm happy that I did not get involved in back

Elliot Volkman: you're welcome.

Alex Love: the and I was like, I remember that.

Glen Hellman: so I tell you the story. So I had a pretty popular blog and It got more popular because of things like Trustify. And what happened was, somebody called me and said, I just saw this guy pitch, and he said he's a Harvard grad, and I know he's not. And so then I just started doing a little bit of research, and digging, and saying, just assume everything this guy says is not true.

Elliot Volkman: Yeah.

Glen Hellman: And you know, peeling back the onion, it just, it was a rotten onion.

Elliot Volkman: Yeah. Oh my God. And to add to that, it was like a, one of those like certification things that anyone gets entry into. It was before people

Alex Love: Harvard Business School online or, you

Elliot Volkman: Yeah. It that. Or was it even that it

Glen Hellman: It was, yeah, it was, it was all you needed was a credit card,

Elliot Volkman: Yeah, exactly. Oh, my gosh. so, so

Alex Love: here is, lie about things that people can't easily check, especially with now, you know, the technology and internet that we have.

Glen Hellman: right? Right. Yeah, it's, it's amazing. The internet, you know, it's it used to be so easy to lie. It's not as easy any longer.

Elliot Volkman: Yeah, absolutely. Fair points. So, I mean, maybe we can kind of pivot back over away from the things that I, as much as I would love to talk about it, uh, that a whole nother conversation and maybe a whole nother podcast of defrauding investors and all that. But yeah, I want to dig more into your background because obviously, again, as a coach, you're interacting with people who are, you know, essentially what would be our listeners.

People who are interested in growing beyond their current capacity maybe they're through like the, the pits of sorrow or death, sorrow or whatever those terminologies we like to use for startup founders. But yeah, I don't know. Can we look back at that conversation that we kick this off with is, you know, you ran into a scenario where obviously.

There are two big names still out there. Yours didn't quite make it. But you know, how did you navigate around that? What did you learn from it outside of like the technology limitations that pulled, pulled you back from it?

Glen Hellman: I'd like to say that I learned from that one situation. But I didn't. So I made the same mistakes multiple times. I will tell you that what I've learned over time is, and what I do from the Maryland instruction side, the NSF side, is teaching people how to do unbiased customer discovery. So had I looked at the job that we were, everybody was doing what we were going to help them automate and do better.

There were sales managers, there were sales people, there were CFOs who would use our system, and everybody had a job and a responsibility. So, I should have documented their job, documented how my, my, my, I would fit in their workflow, and then I should have interviewed. And I should have interviewed. Every type of constituent or type of person who would be involved in the ecosystem and they should have had enough interviews because the salespeople would have told me, no, we'll never use it.

No, we'll. So it is talk to your base. So, and, and, and never stop. So I will bet you that blockbuster talked to their customers after they started. Do you think Netflix knows what their market and what their people want? They have people who are calling out, talking to customers, understanding the trends and constantly changing.

But it's all customer discovery. It's all making sure you have customer market fit and that, and that customer market fit never changes. For instance, in the first startup today, the infrastructure is there that the, at least the technology would have worked. It wouldn't have been a. It wouldn't have been abrasive.

You know, it was, it was a difficulty that if the technology worked, perhaps the fact that the salespeople didn't like it would not have sabotaged it because the value that it gave management was greater.

Alex Love: So are you suggesting as, you know, a founder startup, you are out there pounding the pavement yourself, right? Talking to customers, not necessarily relying on these third party sources to do that. You know, what kind of questions would you go out there asking and how would you sort of formulate that plan?

Glen Hellman: So, so let's look at a hypothetical. Let's say I invested, invented a new a new hip, a hip replacement. Okay? gets used by people who have bad hips, probably people in their 60s. It gets, it gets the actual, so they're the beneficiary. The end users are the surgeon. So I need to look at what that surgeon does and how they do their operation.

Does it make their job better? Do they have to relearn techniques? Is there going to be friction for them to use it? I have to talk to the insurance companies and see, will it get reimbursed? Is it better than the other systems? Is it cheaper? Will it last longer? Will it be more successful? Can I get it through insurance?

I have to talk to the CFO of the, of the hospital. What, what are his economic decisions? And I need to understand, and I need to not talk about the hip. I need to ask them questions about the job they do. So I need to know how do they prioritize things? I need to know how have they entered when you brought in new products before, how have you brought them in? What are your priorities for bringing in new products? You know, what is the priority and what is the. Satisfaction with the current way you're doing things. So, I need to know what satisfaction level is for certain things, and I'll give you a great example of how priorities and satisfaction levels don't match, or are important.

If five years ago I said, How important is it to have a cure for COVID? Everybody'd say, It's a 10 out of 10. And if I said, How satisfied are you with the current COVID cures? They'd say, It's a 1 out of 10. That tells me that's a great market. Ask the same question today. There is no cure. So, how satisfied are you with the cure?

Well, you might say four. Because it's not, and when I say how urgent is it, you might say two. It's not that important anymore. So, understanding both urgency and satisfaction levels, and then figuring out who has the highest urgency, So, you want to, you want to, you want to pick a subset of a market. You don't want to go after an, you never want to go after an entire market.

You want to pick your beachhead market, those who have the ability to pay, a high priority or, or low satisfaction level with what they're doing, um, high priority, but also, are they early adopters? Are they risk averse? Are they do they have a good network when you're, is it a small community where if you get five of them, you can get 100.

So you want to have all these factors and characteristics and pick what's my beachhead.

Alex Love: I think that's a really important orientation. A lot of people get so excited about the product or the service and they go in like hard pitch, right? Like, here's what I got. Here's my idea. It's the best thing ever. And then it fails, right? Because they don't do their due diligence to think about, yes, maybe it is a great idea, maybe it is the next big thing, but does anyone want to buy it?

Does it solve a critical problem? Is it a better mousetrap? So it's really difficult, I think, to get people off of that idea that, yeah, you may have the next best a hundred million idea, but if you don't have the data to support it and you haven't gone out and done your due diligence, it might be a turd.

Glen Hellman: And, and, and Alex if, if you, if you went to an investor, they want to know you're selling to a billion dollar market. But they also want to know it's not going to cost you a billion dollars to attack that market. They want to know that you're in, you're smart about it. So for instance, I have a client who has a software product that competes against Atlassian.

It's a software development product and Atlassian is a gorilla. This is small company. And so when we looked at it, we said, what separates you from Atlassian? What is your beachhead? And we decided highly regulated Secure clients is where they had an advantage. So now, as they go into that market, those people in banks all talk to each other. Those people in, the other thing that happens is the product requirements when they say, Well, we need this feature, we need this feature. Their feature gets stronger and stronger for that specific market. that they are building a wall around and own it. And when they get enough of a market share in that niche, that highly regulated niche.

Then they can start moving into an adjacent market, but you don't want markets are like the 10 pins in a bowling alley. You don't throw the ball at all 10. You throw it at the first pin and have that knock down all the others.

Alex Love: Yeah, that's good advice. So the other thing you mentioned in your initial failure story was, was two things, right? Twofold, you know, failure to do your customer discovery. And then the other thing was technology not sort of meeting, you know, the requirements. Is there, did you think going into the situation that the technology would catch up?

That, you know, the internet was coming, that it would sort of, you know, eventually catch up to you? And is there any time, especially now where we are with AI and all this big technology coming up, do you ever hedge your bets? And put the technology or the product out there and, you know, maybe you do get lucky, maybe the technology does catch up.

Glen Hellman: I, I would not, I, I would say no. So, you know, I did one of the things that made me cranky was I did 10 years doing. Turnarounds. So a VC, there was a local company here called Ikembo. It was my second turnaround I worked on. The VCs hired me. And it was also a mismatch. It was a messaging platform. And there are many products like it now, 10 years later, that do what it did.

It was a messaging platform that worked within Enterprise software products. So anyway, like Twilio does the kind of thing it did back then. But we were never going to make it work if I would not take that kind of risk of betting that the market's going to catch up.

Alex Love: Okay, fair enough. So you mentioned turnarounds, that was a big part of your career. Any critical lessons learned or just common failures you saw and reasons why got pulled in?

Glen Hellman: You know, depending on how you count them, out of the five I did, only one was based on had a management team that was nefarious, that I would chalk up the failures to Danny Boice type nefarious and the guy never went to jail, and, you know, I should have, yeah, which is probably why I got so Vicious with Danny because, when I got there, there were 30 people. And after 30 days, I had to cut it down to 14.

Elliot Volkman: Wow.

Glen Hellman: I had another 1 where when I got there, there were 30 people. And in the first day there were 299 because I got rid of the masseuse, um, who was on salary.

But I did have to stand in front of that group and let them know that there were only going to be 70 of us 90 days now or else there'd be none of us. And none of those had made, none of those people who lost their jobs and couldn't make a paycheck for their families. None of them did anything wrong except for go to work for the wrong company. Most of the time, it's been bad customer market fit, bad product market fit. aNd that's why I'm a big believer in a good, solid customer discovery process before you launch.

Alex Love: Are there any good resources or frameworks that you encourage your students and, you know, executive coaches to take a look at so they can learn a lot more about, you know, how to design that process for their product and service?

Glen Hellman: So, if you are in the state of Maryland, you can actually, anybody in the state of Maryland not just a Maryland alum, can... You can go to our classes that we run just go to UMD I Corps, I, capital I C O R P S. But, many other schools run an I Corps program. The program is designed after a program that's taught at Stanford.

It's Steve Blank's customer discovery workshop that we teach. So, you know, read Steve Blank's stuff. Look at Steve Blank's stuff.

Elliot Volkman: Love it. So I think obviously customer discovery, first of all, I got to say, I love that positioning. Usually you hear product market fit or validation of a solution, but The crux of it is customers. Just the positioning alone is so much nicer than what we typically hear, especially because I don't know, Alex, you probably live and breathe it too.

So you probably hear that kind of stuff all the time. But positioning is everything. So I don't know. I think that has a nice, a nice coat of paint how it should be

Glen Hellman: And even if you have the best products and sliced bread, you know, we didn't attack Germany by throwing people all, you know, we didn't, you know, we went on a beachhead then we expanded, um, in world war two. It's, it's the same thing. It's not just do I have a great product, but it's where do I start because I have limited resources.

What's the limited beachhead that I can attack, have some success and protect. And then use that success to build to the larger total addressable market.

Alex Love: Yeah, I mean living in the government contracting world. That's my whole approach, right? I can't service the entire government I wouldn't want to try but we we have to know our customers, right? we have to to find that one office or that one person or that like Get very intimate and customer intimacy with that person in that department to help them figure out How do I solve this specific problem for you without pushing products and services, right?

Like I'm just here to help you Do what you want to do and if it's my company and if it's this product and if it's this service, great, but if not, like You know, how do I better serve, you know, the customers who are the U. S. citizens at the end of the day? So I love that as a government marketer, cause that's my entire world.

Glen Hellman: And I bet you, you don't, you, you either do DOD or you do civilian and you have some kind of sector experience. And there's a lot of reasons why you want to focus on that sector.

Alex Love: Yes, we do not do both. DOD and civilian do not, it's not the same. It's definitely not the same. We focus on the civilian side. That's where we work, but yeah, absolutely. totally different markets.

Elliot Volkman: For the private space, we are in the same scenario. So whereas you have like civilian versus DOD, it's more like, I don't know, mid market startup versus enterprise. And that is usually where I see like cybersecurity companies absolutely fall apart. They will either start at the enterprise level and being able to go up against incumbents that, right.

It is just like pulling teeth and then they always try to position it like, Oh yeah, just rip this out, put us in. I'm sure that'll go over well. Never has ever.

Glen Hellman: And, and, and one of the things, for instance, in cybersecurity is how do your, how do your customers buy? Will they buy from an independent vendor or do they have a outsourced security company that run, that, is their outsourced, they run their security and you've got to sell to them. So part of customer discovery is not just understanding, do I have a good widget, but also how do people buy widgets like this?

Elliot Volkman: That is so perfectly said. I mean, that that's our sound bite right there.

Alex Love: How do people buy and how long too? I mean, maybe that's just me again in government marketing, but our sales cycle is like 18 to 36 months, right? It's long. So, you know, what works in the private sector and all the attribution models, it just doesn't work. There's just too many people, too many touch points.

But we need to know like, how do they buy on what vehicles? What's the timeline? Who currently holds this work? How do we solve this problem? And how do we design the best team to put ourselves up there and be the differentiator to win? Again, at the end of the day, it's the people that we're really selling.

It's not necessarily a product or service. It may not be any different than our competitors but they trust us. You know, we're the people who can do the work the best.

Glen Hellman: And one of the big issues you have when you have a long sales cycle is how do I know if I have the right sales person?

Alex Love: We typically don't. Unfortunately, salespeople come and go.

Glen Hellman: Yeah, another thing that we spend a lot of time with that I, with, with my clients is how do you hire? What's the contract you make with somebody of is what I expect to see this is the activity levels. I expect to see this is how I audit those activity levels. So you really need to understand the metrics of for instance, what are the stages of a sales cycle? Does a person have enough deals in each stage of the sales cycle where, you know, they're going to go through and then ruthlessly, ruthlessly Don't, if it should take two months to get from this stage, from the, we gave them a dump, we understand what their need is to, we're about to give a demo and a presentation to the team.

If that's been in that stage for three months, not a deal anymore. Get it your pipeline. And now your pipe, you want to keep, you want to keep your pipeline in each level full.

Alex Love: Yeah, I think that's a mistake a lot of people make is sunk cost, right? You know, we've tracked this client for so long, we've been trying to get this deal through this phase, it's gonna come, maybe they'll move the end of the year, a new quarter, like whatever the excuse is, right? But not a lot of people sort of do that grooming of their pipeline appropriately.

Glen Hellman: salespeople with happy years. You don't them have happy years. You want to say, you know, maybe it will come through, but it doesn't count for you right now. You need to get another deal in this stage of the pipeline and it needs to move in this amount of time.

Elliot Volkman: think if we look at the lens of our current environment where large entities are currently going through swaths of layoffs reflecting back on something you'd mentioned, not, you know, a few moments ago about trimming, basically trimming the fat of cutting the teams in halves. How do you, you know, walk a founder, especially a first time founder through doing that kind of scenario?

Obviously you're. Educating them on how to, you know, monitor and provide key metrics that they should track people against. But, you know, not every founder has fired someone before, let alone let go a huge,

Glen Hellman: So the hardest decision to make is you have somebody who's really good at their job, really good, but they're not a cultural fit, makes the rest of the team not, that's the hardest thing to counsel people out of. So when you're hiring, There's four characteristics you hire for, and I'm going to go from least important to most important.

Least important is experience. Unless you need them to be productive the day you hire them, it is the least important. The next is cognitive ability. Do they have the smarts, the, the, Ability to ask questions. Do they, are they logical? Do they think fast? So cognitive ability. The third one is personality traits.

So if you guys gave me a CFO test, and I only had to work on it for 20 minutes, I'd nail it. I know how balance sheets work. I know, I know cash flow statements. I know all about it. I can do it. But if you made me sit down and do it for two hours, not only would I become very cranky, But it might, I'm not detail oriented.

It's, it's against my wiring. So hiring people, which is a mistake we make, often hiring people that don't, that aren't wired for the job we've asked them to do. You don't want a salesperson who's a pleaser. sounds right, but you want a salesperson who's going to ask hard questions most of the time.

Every sales job requires, but you don't want a pleaser. You want somebody who's going to ask uncomfortable questions. What is your budget? So that, and the most important is, have you defined your culture, and is this person a cultural fit? Because teams that have a cultural, culturally fit teams, teams that have a good, strong culture, and they've hired for culture, will outperform the best individual players.

A group of individual All Stars every day.

Elliot Volkman: totally agree.

Glen Hellman: the other thing about that. Everybody says, Okay, Glenn, so how do you know if they're a team? How do you know if they're a cultural thing? And the answer is, You don't say, We only hire team players. Are you a team

Elliot Volkman: a family.

Alex Love: I was just going to say, and we are formally.

Glen Hellman: So what you do say is Give me a situation where One of your teammates, was failing. What'd you do about it? You want to know that somebody is a problem solver. Give me a situation that one of your customers was, was so angry. Things had failed. They were going to leave. Tell me how you dealt with it.

You want to ask situational questions. that give you some idea of, yes, this person is a cultural fit.

Alex Love: So here's a spin off question because I love that. So culture is always evolving, right? And so we're kind of in the middle of this now, right? Leaving startup, going into mid market. The kind of people that succeed in a startup. environment may not make it in the mid market, right? There's a more rigor and process and you sort of have to, you know, start to play and cross collaborate a lot more.

And then that goes, you know, tenfold over in the enterprise level where you've got specialized departments, lots of red tape, lots of other things, processes that you need to follow. How do you evaluate a candidate who may be able to scale all of those and, or, How and when do you advise founders who may be really partial to someone who's been with their company for, you know, the first 10 years, the, the startup phase, and now are actually a problem in the mid market phase because they no longer fit the culture that they need.

Glen Hellman: um, you have to look at your culture and constantly evaluate And people, if your culture is strong and if you enforce cultural values, people will opt out if they fit. So, you know, so but you have to change the culture. So when you first start a company, most companies start on a loyalty culture.

Because you can't pay. You're very that the people stuck with you you really owe them. But, but once you get to a mid market company, once you get past small business and you start getting real profitable and growth, uh, loyalty culture becomes toxic because. You want people who perform and you want people to see that everybody, you gotta move to a performance culture.

You want everybody to see that there are no laggards here, that we're a performance culture. So culture constantly evolves. It is the most difficult thing. It's very situational. There's no pat answer. But you always have to ask yourself, just like, do I still fit? Does my product still fit in the customer environment?

Is my culture still a fit for who we are in the market?

Alex Love: Yeah, yeah, very true. I don't know that I'm a enterprise person. I like the chaos of the small business and mid market size, but you know.

Glen Hellman: Yeah,

Alex Love: Self identifying is important. As you said, I would opt out of that, right? I've been in big businesses. fine. It gives you a certain work life balance and other things that, you know, you can pursue, but I think you need to know yourself and if

Glen Hellman: absolutely. You know, there are people who don't mind bureaucracy. There's people who don't mind glacial change. There's people who don't mind politics, you know, then there's the rest of us, you know, the startup, they're new startup folks.

Alex Love: Everyone on the call, living the chaos. Absolutely.

Glen Hellman: I'll tell you I look at my career, I started in startups right away, first thing, got bought by Raytheon and I made it a year there. And then I did a bunch of other startups. Most of them failed, but they were fun. They were invigorating. And then I did this thing called call technologies, which we were there six years, made a lot of money, sold it for a hundred million cash.

We did progress, sold it for three 60. When we got bought by 3Com for a hundred million dollars cash, I had to work for 3Com for a year to get my earn out. And I was a general manager of a software division with about 300 people working for me. I had less. autonomy. I had less authority, autonomy, less impact.

I hated it. The day after my contract was over, I was gone. So, and that's when I started my turnaround career, which was great because the longest thing I ever did there was two years. And then I got bored with that. So coaching, I'm in a new company every day, two or three every day. I'm working on new problems.

So I'm a chaos junkie.

Alex Love: That's a good point. A lot of these sales come with, you know, the golden handcuffs of, you know, we need this person to execute for X amount of time. Do you find that those are beneficial or, or, or, you know, exactly what you said, right? You see a lot of people sort of do the bare minimum for the time that they're sort of allotted to, to take their money and then I'm out.

Glen Hellman: So I, I, I don't think most people will do the bare minimum. If you've got an exit like that, you've got this competitive spirit where you, for me, it was the competitive spirit that I wanted to know I could make a difference and it was not making a difference that got me out of there. It being able to make a difference.

And it was also the backbiting and the jealousy of other, you know, groups. It was all the. All the, the problems of, I think it was Malcolm Gladwell, not a big fan of Malcolm Gladwell, but in his first book, he talks about humans can only really work well as a team and identify with shared values up to a hundred people.

And it's something in our brain, some thing in our brain that sort of wires us that way. And once you get past a hundred, you need to figure out how to... Get people so that they don't do the backbiting and stuff. And most corporations don't do that.

Alex Love: Yeah. I haven't heard the hundred rule, but there's something about like personal friends, right? Like. The average person can only have like 12 connections or 20 meaningful connections in their life before it gets, you know,

Glen Hellman: Yeah. So in that book, it's, it's interesting. Cause he talks about like every animal, there's a thing in our brain that you measure it and you can tell how many people they have. So like porpoises are 40 and we're hundred. So what was the name of that company? Gore Tex, Gore, Gore Tex company. They used to, they build a plant.

It'd have a hundred parking spaces in it. Once the parking lot was filled, they create a new division. So, you know, at first it was it was used as fill for insulation for jackets, coats. Then they start a new one. It became, they used it for bulletproof vests. And they create a new one. They started making helmets.

Then they did a new one in it. They even did floss. So, like, most floss is based on their product because it doesn't break.

Alex Love: Interesting product evolution for sure. Who knew floss came from the insides of

Elliot Volkman: Hey, I mean, if you compare it to the ball company with the ball jars, they're a DoD contractor, which is just a really wild journey. Yeah, seriously. I think they actually licensed the name to whoever manufactures the jars now, and they're primarily on the DoD side, or whatever they do.

Alex Love: Well, I think we're coming up on time. So, I guess this is the part where we ask you, like, what would you like to sort of boil it down to, right? If you could sort of gift our audience a final piece of advice or just big lesson learned across your, you know, very diverse and illustrious career.

What would you say to our audience and any upcoming or current entrepreneurs?

Glen Hellman: so what I'd say is you may be very smart. You may be very intuitive. You may have a lot of EQ, talk to people, challenge what you think, get real product, make sure you have product market fit, talk to customers, talk to people in the ecosystem, and also, you know, get accountability buddy. Don't just go get somebody who has no ulterior motives.

No, your wife has an ulterior motive. Your husband has an ulterior motive. Your CFO, your marketing VP, everybody has an ulterior motive. Find somebody who you can be accountability, accountability buddies with.

Alex Love: Neutral parties.

Glen Hellman: help you. If you help me,

Alex Love: There you go. I love it. Great words of advice. Well, thank you so much, Glenn. This has been a cool blast from the past and, and learned a lot more about other pockets of your life and your career that, you know, we hadn't intersected in. So we really appreciate you taking the time today to talk to Elliot and I about just, you know, life and careers and startups in general.

I learned a lot. I had, I had fun in this conversation

Glen Hellman: I enjoyed it as well. Happy to do it. I'll do it again.

Mastering the Art of Failing
Mastering the Art of Failing Podcast
Join your hosts, Alex Love and Elliot Volkman, as we dismantle the stigma surrounding failure and empower you to transform these challenges into opportunities on your own journey forward.