Corey Spitzer on Becoming a Fractional Executive, Authentic Confidence, and the 20-Minute Disagreement Rule

In brief: Corey Spitzer (flyhighventures.com), a fractional CTO and startup advisor with over 20 years of experience in software engineering, joins host Dan Freehling (contempusleadership.com). Corey and Dan explore the dynamic environment of startups, emphasizing the variety and high-impact nature of the work. Corey discusses the advantages of being based in Omaha, Nebraska, highlighting the supportive and tight-knit tech community. He shares insights on the challenges faced by non-technical founders and the importance of fostering empathy between business and technical teams. Corey also explains the concept of fractional executive roles, offering advice on building a consulting practice and the benefits of working with multiple businesses. The conversation touches on the significance of team culture, the value of improv classes for personal growth, and the importance of self-confidence in leadership.

Recommended reading: “How to Help Underperformers” by Luca Rossi.

Dan Freehling (00:00:01):

Welcome to Forward Looking Leadership, a podcast for visionary leaders building future ready organizations. I'm your host, Dan Freehling. I'm the founder of the coaching and consulting practice, Contempus Leadership, all in for the social impact leaders you want in charge. I'm honored to be joined today by Corey Spitzer. Corey is a fractional CTO who works with early stage startups to define and execute their product roadmap and strategy, revamp their software development efforts, and ensure people, processes, and systems are set up for success. Corey brings over 20 years of professional experience in software engineering with the last decade founding or working with startups. Listeners, you're in for leadership lessons at the intersection of people and tech. Thanks for joining me on Forward-Looking Leadership, Corey.

Corey Spitzer (00:00:43):

Yeah, thank you.

Dan Freehling (00:00:44):

Yeah, appreciate you taking the time and being here and sharing your insights with listeners.

Corey Spitzer (00:00:48):

Yeah, this'll be fun.

Dan Freehling (00:00:50):

Absolutely. So first, can you please share what you're up to at Fly High Ventures?

Corey Spitzer (00:00:55):

At any given time? I'm working with anywhere between two and five startups usually, and that involves anything from developing code myself or technical project management or more advisory consulting about processes or cost projections with cloud costs and things like that, or interviewing and hiring developers and things like that. So I plug in any number of ways.

Dan Freehling (00:01:22):

Yeah, really interesting set of skills you bring to these companies and startups. And on the startup note, what draws you to early stage startups in particular?

Corey Spitzer (00:01:33):

Well, I think I'm really drawn towards variety, which is, I mean, it's sort of meta because not only am I hopping around a lot of different companies that are offering different products and services with different revenue models and different teams, but within a startup, everybody has to wear a lot of different hats. So I found myself writing code for the same company I'm manning a trade show booth for, and I enjoy it all. I like building companies as much as I like building apps. So there's the variety, the high impact, high visibility, kind of healthy pressure there, managing chaos, fast-paced environment, all that, just everything all rolled into one.

Dan Freehling (00:02:19):

Yeah, you just hear it in your voice. It sounds like the chaotic environment is fun for you, not overwhelming as it might be for some people.

Corey Spitzer (00:02:26):

Yeah, yeah. I mean you get used to it.

Dan Freehling (00:02:30):

You're also in Nebraska or in Omaha, so how does that affect your lens on technology not being in Silicon Valley or one of these other major tech hubs around the country?

Corey Spitzer (00:02:42):

I haven't really lived in any of those areas. I grew up in the Midwest. I've kind of stayed in the Midwest, grew up in Illinois and just hopped a couple states over. But from everything that I have read, I mean Omaha and we've got the capital of Nebraska Lincoln in an hour away. I mean, there's a lot of crosspollination between our two cities, and it's always the case that you can always ask somebody for coffee that you don't know, and I've never gotten a no for that question. And similarly, anybody, any stranger in our startup ecosystem can ask me for coffee or lunch. I've probably never said no. And we've got, even though Omaha is half a million people, we have a tight knit community and it's really easy to almost everyone and a lot of people trade favors and they help each other out.

(00:03:39):

I would hope that it's similar in Silicon Valley and Austin and Denver and so on, but it's really hard to say. We're also middle of the country and it's traditionally been lower costs of living here, so that works to our advantage in a lot of cases, especially with shipping. We can ship anywhere packages from the middle of the country to the coast, and that comes to play with a lot of logistics companies and so on. But yeah, we're not as mature as those other startup communities, but we are definitely, we've got some institutions going on as startup accelerator, some very good entrepreneurial events that attracts people outside the region. There's a lot happening.

Dan Freehling (00:04:23):

That's really great. What are some of the entrepreneurial events and tech community events that you're involved in there?

Corey Spitzer (00:04:30):

So we just had BarCamp Omaha. It was earlier in August, and we've got Nebraska Startup Week happening second week of November, and that's led by kind of our main journalistic outlet, the Silicon Prairie News. And it's a whole suite of events, just like Denver Startup Week or other startup weeks, and it's your typical, really meaty set of talks and good networking events and collisions and serendipitous, let's grab coffee and let's find a quiet corner and talk about your business and things like that. It's really nice.

Dan Freehling (00:05:15):

Yeah, it sounds that way. It sounds like a really great community and very friendly and welcoming too, so that's really cool to hear.

Corey Spitzer (00:05:22):

Approachable.

Dan Freehling (00:05:23):

So if somebody was considering either founding a startup or joining a startup as a staff member, what advice would you give them?

Corey Spitzer (00:05:33):

Well, so I tell you, I help startups interview and hire mostly software engineers. And a lot of times we'll look at their resumes and we'll say, oh, there's not a lot of startup experience on here. Do you know what you're getting into? I usually lead with the fact that traditionally startups don't have the same kind of resources and budgets that larger corporations have, and it's more intense if you're joining a startup, especially in the earlier stages, not only are you going to be a large fraction of let's say an engineering team or a department, but you're going to be a large fraction of the entire company. So I regularly help hire the 10th employee, which is going to be 10% of the company. That means you're going to have direct impact on how the product and services evolve and your decisions are going to be very consequential.

(00:06:29):

And at the same time, you're going to have direct access to the top leadership and you're going to have an ear to the strategy in real time as it forms and what a pivot looks like, and you're going to talk to the other departments and see what sales is like. And in a startup, a lot of times everybody can bring in sales leads. So you're really, you just get immersed and you hit the ground running and yeah, there's chaos and there's stress and intensity, but you see a lot of things in a short amount of time relative to a larger corporation where you're just the thousands employee.

Dan Freehling (00:07:10):

That makes total sense. You're not just kind of replaceable cog in the machine there and it's going to keep on rolling fine without you, and you have a very defined scope of work. This is like you're all in it. And any employee can make or break a company at an early stage. And just having that access to the executives or being able to be an executive yourself is just a cool opportunity.

Corey Spitzer (00:07:33):

And the great thing about startups is if something isn't working, let's say process wise, the turnaround time to make a change is super quick. We can as let's say an engineering group, we can decide, you know what? We're going to change our process. We're going to do things differently Starting today. You don't always have that option at larger companies with more processes and bureaucracy and so on. Similarly, if you need a new laptop, you'll get it in the next couple days as opposed to next couple of weeks. So that agility, that nimbleness not only is one less thing to worry about, but is also absolutely needed because not only are you building a product, you're helping build a company as an employee of a 10 person startup let's say, and you have to move fast. You have to learn fast, and you have to respond and figure out what you're doing and where you're going.

Dan Freehling (00:08:34):

Yeah, I can definitely see how that's an exciting environment to work into with zero, close to zero red tape and you're just going and you're all in for the same mission and building the whole company as well as the product. It's a cool sounding thing to hear about, and I think for the right personality type, something that would be really appealing.

Corey Spitzer (00:08:53):

Yeah, I think everybody's pretty much center stage when they're in a startup.

Dan Freehling (00:08:58):

So as a CTO and advisor, you advise a lot of non-technical founders. What are some of the common challenges you find that non-technical founders in particular face?

Corey Spitzer (00:09:09):

In larger companies, especially maybe like 20 or more employees, there seems to be a lot of times a disconnect between the business side of the house and the software development side of the house because it's different DNA to be kind. And so what I like to do is in larger companies when culture is not maintained, you get a sort of tribalism between departments and you've been there. So what I try to do is foster some empathy of the thousands of micro executive decisions your engineers have to do. And similarly, on the engineering side, we have to be empathetic to the challenges of the business side and all the grinding it takes to do marketing and sales and results aren't guaranteed and everything like that. And so I think the first order of business a lot of times when I come into a company is make sure that there's empathy and recognition between the roughly two sides of the coin that compliment each other and make sure that everybody else's efforts are valued.

(00:10:27):

And then we can start talking about how do we communicate, how do we speak the same language? How do we do very, when you have a team that has very deep technical expertise, how do we master the art of the executive summary to provide enough details to get support and buy-in for certain, let's say architectural decisions in the software or maybe the way that we're going to build this new feature has some impact on the user experience that the product manager needs to know about, and that's going to bubble up to how do we speak about this in a sales conversation? So it's all interconnected and like I said, first order business is to realize everybody's interdependencies on that and then get 'em communicating and then make sure we're all rowing in the same direction. We're not overselling, we're not underdelivering everything all at once, all the time.

Dan Freehling (00:11:28):

That empathy is really coming through and being able to walk in the other side, choose a bit and just know, yeah, it's not like the business side of the house isn't doing anything valuable, they're grinding. It's all looking at all of that. And then conversely, it's not like the tech people are not doing anything valuable where they're really the ones who are going to be delivering the promises and the product here.

Corey Spitzer (00:11:50):

Yes, I think it's a naive thing, sort of discount or to put your department on a pedestal as maybe the most important thing in the company. Everything has to work well for the whole company to work well and deliver.

Dan Freehling (00:12:08):

There's a concept that I think came out of Korn Ferry, which is one of the big consultancies called enterprise Mindset that I like a lot. And it's exactly that idea that it's tempting to always be looking out for just your department and your people, but to really flip that switch into a real enterprise or executive mindset, it's shifting it to looking at the whole business and what's the best decision not for engineering, what's the best decision not for sales, but what's the best decision overall and how do we do that? And it sounds like that's imperative for success at a startup.

Corey Spitzer (00:12:43):

Yeah, absolutely. I listened to a podcast episode, I'm sorry I can't remember the name of it, but there's this mindset similar to what you're talking about of every other department that you interface with is like an internal customer. And at my last full-time gig, I was VP of engineering leading a team, and we came up with some team core values. We had company core values, but we had lost a couple of people on our team and we needed to rebuild and hire some more people. And so it was just me and this other guy, and we ended up hiring three more. But before we did, we sat down and we said, Hey, we need to write down and codify what is it that makes us work so well together and use that as a guide to hire more team members. So one of the core values that we came up with was service to others because we had such a good relationship with the sales department and we were always in concert, they were always checking with us.

(00:13:41):

We called it a tech check to make sure that they were saying the right things and we were delivering something that would empower sales so that they can get more commissions. And so everything, we get some really good successes as a whole company. So that worked really well for us just to say, Hey, we are going to serve sales. We are going to serve customer success so that whether it's tech support or customer service, they have the tools that we can build internally and vice versa. They're going to respect us back and have our backs. So I think that is something that is almost universally applicable across any company.

Dan Freehling (00:14:30):

Yeah, that's a great thing for people to add that there are toolkits of, I love the tech checks concept and how does this make everyone working in the same direction and better off? And you're right, it's like if the salespeople can get better at understanding the tech, then their commissions are going to increase. I think that's just not that intuitive for a lot of folks too.

Corey Spitzer (00:14:50):

Oh, sure. Yeah. And that's another thing with in startups, stock options are more prevalent as an incentive, and it's actually, it's kind of a win-win because like I said, startups don't necessarily have all of the war chests of cash that big corporations have, but having stock options not only mitigates that issue, but it incentivizes the employees themselves to have an outsized payday if the startup does well. So it's a great way to just generally attract talent that punches above your weight.

Dan Freehling (00:15:30):

It's such a good point, and I think that having an equity model is a great way to, it's a very businesslike way of thinking, but it is really helpful in all of the other kind of empathy and collaboration and teamwork and all of that. If you're structurally set up for that and people are not just focused on getting their paycheck or their department's budget increased or whatever it is, that can go a long way. I think it's a really great point.

Corey Spitzer (00:15:58):

I think there's an emotional component to it. You want to have emotional buy-in into the mission of the startup because especially with software developers, I mean, they're driven by a few common things like learning new technologies, playing with the latest technologies purpose, and it kind of goes hand in hand with, Hey, I believe in this mission and because I am a large percentage of this company, I can be extraordinarily impactful to that mission that I believe in. And if we all do our jobs well, then there's a really good monetary ROI if the company gets acquired or goes IPO or what have you.

Dan Freehling (00:16:41):

It's a really great reminder for people too. And I think that it's not something you hear outside of the tech space, a lot of software engineers being really purpose driven, but it's obviously true. It makes a lot of sense. And just like everyone else in the business, if you can get people bought into it, bought into the mission, bought into the purpose, and sharing in the rewards for it, it's just going to go a long way and making people really give their all for it and then prioritize the right things for the right reasons, not to just maximize their own individual gain or their own parochial kind of department gain instead of the whole enterprise.

Corey Spitzer (00:17:14):

And I think there's a large chunk of software engineers that are driven by when a customer's eyes light up because they're using a feature you built for the first time and you get that feedback, at least for me, that's kind of a magical moment. And in a lot of companies, they are so many layers away from a customer, they don't get that feedback. Now, not every technical person wants to interface with a customer, but to know that the work you did is not only being used but appreciated, that is a powerful force

Dan Freehling (00:17:52):

Seeing that impact and that craft, and you mentioned being able to have access to the latest technology and really think in a big way about this and play around with it and make something different, innovative tools that meets the customer's needs as a real opportunity. I think people forget that a lot when shaping jobs, and it's so much more than just the remuneration for it. It's a big part of it, but yeah, what is the actual impact of the work? And people see this, can they be learning and growing as they're doing it and thinking that through and designing a company, designing positions is key.

Corey Spitzer (00:18:29):

Exactly. Yeah.

Dan Freehling (00:18:31):

The fractional executive concept is getting much more popular. And I know I've talked to several people who have been interested in pursuing this either as people leaving a corporate job or adding it on to their consultancy. I'd love for you to share with listeners what it's like working as a fractional executive and any tips you would have for others who are interested in finding similar opportunities.

Corey Spitzer (00:18:56):

It's not necessarily that different than being a freelancer or a contractor or an employee, it's just I guess a different flavor, at least for me. Let me put it this way. There was a point where I had been around the block enough, and I feel like there's a reason why the average age of a first time entrepreneur is about 39 40, and it's because, at least for me, I speculate that you enter this phase where you have seen enough and you have a certain amount of confidence in yourself, and you've been through enough repetitions of certain skills, exercising your skills and job, and it's almost like a light switch goes off in your brain. It's like, oh, I'm ready for this. I can do this. I'm old enough, wise enough, experienced enough. And so it's really just I had this sense of, I kind of know how a lot of things work and I know how this would apply to potential clients.

(00:20:06):

I see a lot of other startups happening around me, and as I'm just talking to people and sharing some free advice, it's clicking and I'm seeing like, oh yeah, you're kind of like the next generation behind me. Well, let me tell you what I did five years ago or 10 years ago. This is how we solve that issue and this is how we address that problem. And it seems really similar to what you're going through right now. So I think there comes a time in your career when you have built up enough experience that you can give really powerful advice to people as most likely. We have gotten really good advice and mentorship earlier in our careers, and we still do. Everybody can learn from everybody. But I think that there just, I don't know, at least for me, there was a moment in time where it's like, oh, this doesn't seem like a foreign concept.

(00:21:03):

I'm ready this readiness feeling. So that's not to say that I've never met a software engineer that isn't doing something they've never done before at least once a month. So I still fall in that category. I'm still doing things I've never done before and still expanding out of my comfort zone and things like that. But I think at least with startup communities in general, the way I run into people and find clients is I show up, I keep showing up, I become a familiar face, I give free advice. I was just working. I just spent a couple hours helping a guy with a spreadsheet issue and that's not a couple hours is not worth spinning up a contract and things like that. It's just kind of a good first mentality and people get to know you and what you're capable of, and then when the timing and the need aligns, then they know who to call. So that's generally how I've gotten clients is just being in the community. I expect to do a little more traveling next year to other startup communities and go to other events and just keep meeting people. And like I said, if things needs align, then I'm happy to explore more, but I'm not there for a hard sell, let's say, or an aggressive sale.

Dan Freehling (00:22:25):

Yeah, this is just great advice for people too, and I think I like how you put this in the broader bucket of a freelancer or consulting business rather than some of the ways you would traditionally ascend to an executive role through promotion within an organization or being headhunted from outside of an organization. And I think that's helpful for people too. This is all of the ideas and concepts that apply to developing business as a freelancer, as an independent consultant, that kind of a thing apply to this. And you're so right with the giving first, sharing your expertise, being super generous, and then the right kind of work will fall in around that. That's what I've noticed too in building my practice and it sounds like we're pretty similar in how we approach that. It's just helpful for people to put the fractional executive in that framework, and I think it'll be really useful for them

Corey Spitzer (00:23:20):

And not to downplay the benefits of climbing a corporate ladder in the traditional sense. Sometimes I do think that maybe I should have done that, but I do think that there is an advantage to the fact that I am working with multiple businesses sometimes that are just completely unrelated to each other at the same time. And so it often happens things that I am figuring out and learning in one business directly applies to another one sometimes in the same week or in a very close time span. And so over just the last couple of years, there's a lot of commonalities in the challenges of early stage startups, small businesses or growth stage startups, whether it's like I said, managing a team or figuring out how to bring AI in-house and doing some research. So some very tactical learnings, let's say with ai, some code that I wrote for one company, the learnings along the way, I can just be valuable right out the gate for the next conversation that is even remotely similar.

Dan Freehling (00:24:35):

Yeah, I've noticed the same exact thing in my business as well, and you mentioned earlier about that kind of coming to a moment in your career where you're looking around and you're like, wait a second, I know a lot of things here. I can pull them together from people and this can be really valuable. And it's kind of like a really fast switch, and I've noticed that in, and you're so right about working with multiple different businesses and different people and the learnings from one applying to the other. I think it helps to get out of the bubble of one person or one company's way of thinking and to start seeing problems and opportunities as much more common or universal. And there's some different ways to approach them from this kind of way of thinking. There's some different ways to approach from this kind of way of thinking, and it makes the problems less extreme, I think, in my mind and much more solvable and it's, there's so many ways to go about this. There's not just one way of thinking.

Corey Spitzer (00:25:34):

Exactly. Yeah, and here's an example. So I had two clients late last year, roughly within a few months of each other. One I was brought in to do a culture assessment because their dev team was not very healthy. So I spent a few weeks doing one-on-one meetings with everyone and figuring out what individual's career goals and their strengths and their weaknesses were, compare that to what the company needed. I wrote up a big old report and I influenced reorganization in the new org chart. Then a couple months later, I did a similar of job for another company. It wasn't about culture, it was about process. And it wasn't to inform an org chart, but this particular company was very flat. They did not want to be hierarchical at all. They wanted to cultivate leadership in their teams and have their teams sort of self-directed with some very light management touches from their CEO and CIO.

(00:26:43):

It was completely different than any other company I've ever seen. But now I have that experience and I can compare and contrast and cherry pick from those two different companies, and I say, well, I saw that working at that company and this other company had another way to look at the same issue. So every company, even though there's some very formulaic commonalities, you always have to adapt to the particular culture that you're coming into or the particular products and how they address the market in their own way. So it's kind of like, I don't know if you're familiar with agile methodology for startup development, but every company, even though it comes from the same manifesto, every company kind of does their own spin on it. And the more iterations of that I see, the more ways I get this sixth sense built up of what's going to work here and what's not going to work so well.

Dan Freehling (00:27:47):

Yeah, I mean you're doing a lot of organizational development work in your own way with this. It's just kind of, it's interesting to hear and it's obviously just so useful even outside of a direct OD consulting space where I come from where it's just as executives and as freelancers doing other kinds of work with companies, how useful this is. I think to the confidence point, that's one of the biggest things I've noticed is that a lot of the value of the confidence of experience comes in being able to call out very limited ways of thinking, or this is the only way to do agile startup methodology that's like, no, no, for a fact it's not. And you can say that with confidence. I think that happens a million times in different settings throughout organizations that it's just there's a point before then when you really don't know if that is the only way to do it. And there's certainly things where there is only one right way to do them, but they're pretty rare, especially when you're working with people.

Corey Spitzer (00:28:50):

I think we're getting at the root of something here with regard to there's good business process in theory in good textbook MB, a way of doing things, and then there's street smarts, and when you're in a startup and you got to get scrappy and resourceful, street smarts book beat a textbook any day.

Dan Freehling (00:29:14):

Absolutely. And I think it's useful to have some of these frameworks and ways of thinking about things and be able to pull from them and all that kind of stuff, but not be wedded to, oh, I read it in a textbook, or This is the way that Harvard Business School says you have to do X or Y or that kind of a thing, and you're so right. I think that's exactly it. It's making it work. And that common sense being a rare commodity these days, the street smarts being rarer than you'd like to see a lot of the time in things without being anti-intellectual or anti academic or anything like that too. I think there's some people that just dismiss that whole cloth and it's like, no, there's lots to learn in this, but it's not the most important thing is does this actually work for this context with this group?

Corey Spitzer (00:30:00):

Yeah, I think a lot of times the way this manifests itself is you'll get a very busy executive who will have a very good conversation with one of their peers at another company, or they'll read a blog post or something like that and then they'll come to the table and they'll say, oh my God, I'm so excited. We should be doing X, Y, and Z. We should be doing things this way. And that's kind of the easy part. The hard part is saying, okay, what are the good principles out of this? Do they apply? How could they apply? How do we fold it in? How do we execute? Does it work for us? Is it right for us? Because good ideas are good ideas, it's just depending on where you are in your own custom circumstances. And it's always good to not be so heads down. I always say, you're either heads down or heads up and you got to make time for both, but there's also a lot of nuance into actually taking a good idea and running with it.

Dan Freehling (00:31:04):

So you focus a lot on promoting a healthy team culture, which I think might be not surprising from everything we've talked about, but might be kind of unusual for people thinking of a stereotypical tech person, team culture being super important to them. So why is team culture so important to you and what advice do you have for leaders in promoting it?

Corey Spitzer (00:31:25):

Well, I think we've all worked in environments where there is not a healthy team culture and I don't really want to do that. And if there's ways I can help companies or prevent toxicity, then I think that's a worthy cause. But also, so I grew up as this stereotypical computer geek, no social skills, very awkward. All I wanted to do was code all day every day. I don't need to talk to people or sell myself or communicate well, I know too much. And so when I started valuing how I came across to people and investing in growth and soft skills and trying different things and then getting better at it, and I didn't have a lot of self-confidence myself, so a lot of things kind of converge for me as I grew up in a very real sense. And I got confidence and I took improv classes, which I cannot say I cannot speak highly enough of improv classes.

(00:32:42):

They are a game changer for anyone no matter who you are. But I started getting out of my head thanks to improv classes and some other things, putting myself in more social situations and trying to communicate humans do real humans do. And so I think I just wanted to be really good at it, and I found myself on reading books on charisma and how to speak confidently in body language and tone of voice and all these things. And once I just sort of, I guess found myself, it's so energizing. I used to be the biggest introvert now I go to networking events and it's super energizing. So I flipped, I guess guess I'm like an extrovert. It's so rewarding and the way that I found that that can come across, I can find some other person maybe with not the best soft skills, maybe they're underperforming.

(00:33:39):

If I can turn that person around, then that is a huge feather in my cap for myself, and that's very motivating. So I think all of that just comes together that I kind of know. I've seen companies where there's good culture. I've seen companies where people actually like their job and they're delivering and they're shipping and they're invested in the mission and they're enjoying the journey of building the products and serving the customers, and I kind of know a few things about how to get that going, so I just try to serve that up, if that makes sense.

Dan Freehling (00:34:13):

Definitely. No, it's really admirable what you've done. What a cool recommendation on improv. My mentor coach actually has just started doing that. She just did a podcast on that and its benefits for coaches, and I think it's obviously just beneficial for so many different domains of getting yourself out of your own head and collaborating with other people in real time and all of that kind of stuff.

Corey Spitzer (00:34:37):

Communication is hard for anybody. But one of the things that I struggled with was, oh, somebody asked me how a certain feature work or some system I built worked, and it's like, oh, shoot, where do I even start? Oh, wait, okay. I just paralyzed trying to construct the perfect story to give them the best scenic route around this thing that I'm trying to describe, but I have to, there was this challenge of real time translation from I can't really talk about function calls and the inner workings of APIs and things like that to this person. So it's like the way it came out of my mouth was very inarticulate, just stop, go pause, interrupt myself, cut myself off, rephrase. Oh no, that's a dead end. It was a struggle. It was just pure suffering.

Dan Freehling (00:35:35):

That's great. The improv helps you in being able to do that and you're able to, I think, take different metaphors and ways of communicating and do them in real time and have it work. Even if you're not sure where you start is going to be a good place to start in the communication. It's like, okay, we're going to be able to do this and get through it and get a point across.

Corey Spitzer (00:35:57):

Yeah, I don't know what it is. It's like this ineffable thing. I can't put my finger on what that skill actually is. It's just, hey, don't think too little, but kind of think ahead a little bit. I don't even know how to describe it, which is the most ironic thing.

Dan Freehling (00:36:15):

No, it sounds a lot like intuition in a lot of ways where you're able to get out of your own head and be in the moment and be able to react and respond in real time and foresee where things are going and be really hard to describe what that entails. But it does sound a lot like intuition work,

Corey Spitzer (00:36:32):

And I cannot, I think a vital factor in that is confidence. I didn't realize this for the longest time, but confidence. I didn't know what confidence felt like, but self-confidence is the bedrock that powers all of these things. And now you got me stuck thinking about how do I describe this feeling? I have this picture in my head. There's an arcade game where you have to sort of hit a little sensor with a mallet. You can't hit it too hard, you can't hit it too soft. That's like you got to find that middle ground of how your brain is firing. Don't think too much, but don't think too little plan ahead, but don't get in your head.

Dan Freehling (00:37:20):

So the head and the heart combined and the intellect and the intuition, and where is that balance to be struck with it? And yeah, you see people going too far in either direction and it's either so kind of woo woo sounding that it doesn't make any sense, or it's so polished and butted up and trying to be perfect that it doesn't actually come across with any heart or anything for real people to pick up on. It's a great metaphor. I love that with the arcade game. That's so cool. So you've also been taking, was it violin lessons or viola lessons?

Corey Spitzer (00:37:53):

I am taking violin lessons.

Dan Freehling (00:37:54):

Violin lessons

Corey Spitzer (00:37:55):

Have been taking violin lessons for 10 years and maybe in another 10 years I'll say sound decent.

Dan Freehling (00:38:04):

What is it that's kept you going for 10 years on that if it's not about joining an orchestra or something?

Corey Spitzer (00:38:12):

I think at one point it was like, well, I'm a couple years in. I can't quit now. That would be lost investment.

(00:38:19):

But I guess I kept watching YouTube videos and I'm like, Hey, it is possible. And I think this applies to a lot of things. Any kind of skill or any kind of business, you see somebody that has done the thing you want to do, there's a path from where you are now to what that person is doing. You just have to figure out every little baby step along the way. And I remember there was a time when I thought about quitting and it was because I couldn't move my middle finger like an inch, an inch more because when you're playing violin, you're using muscles. You never have to use individual finger muscles, and so you kind of have to work out your fingers. But I'm like, well, this has to be possible. Every good violinist can move their finger. Every good violinist can make all your little muscles and the angle of the bow and the weight on the bow and all these little hundreds of little tension points work. So I know it's possible. I just have to get there and what's the next step to get there? So this is very much a enjoy the journey. I'm on the slow path, but I'll get there. I'm in no rush. It's

Dan Freehling (00:39:38):

Not about the outcome in this case, it's about learning and growing along the way.

Corey Spitzer (00:39:43):

It's kind of like it's a little sprinkle of variety in my life. I think it's important for everyone to do something that is completely different than anything else they're currently doing.

Dan Freehling (00:39:55):

I think that's so right that it's admirable again, that you're putting in the effort to do this. It's really cool On the confidence piece from the previous answer, I think that it's really sticking with me as something key here, and I think there's a misconception from a lot of people of what self-confidence looks like. It's not like the bravado kind of confidence, the fake confidence. It feels like accepting and knowing who you are and what you want to be doing, and then not being afraid to sometimes look foolish to people if you're doing that or try to be always putting on fronts or always posturing for that, but really having that peace with who you are, what you're able to do, what you're not able to do, and that's what it is.

Corey Spitzer (00:40:42):

I think you're absolutely right there. You have to remain authentic. You can't just fake, you can't follow a formula, the confidence formula and say, speak like this and all of that. I think the feeling of confidence is you have a very nice bedrock that you're standing on. You're standing on solid ground and you can handle whatever comes your way. And you're also very comfortable and secure for asking for help and saying, I don't know that thing. And hey, you're going into some uncharted waters and you have all the tools, or you can acquire all the tools by being resourceful and thoughtful to navigate those waters. It's just that feeling of no matter what happens, I can deal with it.

Dan Freehling (00:41:29):

So well said. I work with leaders a lot on this too, of not feeling like you have to pretend to know everything. That would be ridiculous. At a certain point. You can't know every single thing that's going to be happening, but showing up with the confidence of let's figure this out, being in that way of being is something that is much more appealing for other people working with you and actually shows that you have more of this realistic confidence in these realistic skill sets than trying to pretend to know every single little possible thing.

Corey Spitzer (00:42:01):

And now that I think about it, this security, which the opposite of insecurity is absolutely needed, you need to project that to influence a culture that you're trying to influence because by saying, oh, I don't know that thing, or Can you show me how to do this process or show me this tool? You are signaling to everyone around you that, Hey, it's okay to say those things. It's okay to not only admit you don't know somebody, but something, but to ask for help and assistance and really savor the fact that this is the result. I asked for help. You gave me help. Look everybody, this is how you asked for help, and now I know things and I'm so happy about this and look how happy I am. I mean, not literally, but I think that plays a huge part into just general leadership.

Dan Freehling (00:42:55):

It's how you demonstrate and promote a learning culture, a culture of collaboration in a true sense and not a culture of coverup or a culture of bravado or resource hoarding or any of this kind of stuff that really just throws entire organizational cultures off. And by demonstrating that as the leader, and it's not saying I'm stupid, I don't know anything. It's saying for the things that we don't know yet, how do we go about figuring that out and respecting people and trusting people to be part of that and showing that vulnerability as a leader is key.

Corey Spitzer (00:43:28):

And I guess if I was secure with my thought process, I would be very open about it. I would say, Hey, this is where I'm thinking about this problem. And hey, guess what? I'm going to provide some evidence and some backing behind this. This comes from past experience and I'm super transparent about how I'm strategizing in front of my team. Then that's another way that's the opposite of say information hoarding because I am playing politics or I'm being insecure about, well, we can't let that other department know what we know or release that data or anything. So I guess if you're open and transparent with how you're thinking and strategizing about things and how you're approaching problems, then that implicitly invites people to voice their own opinions and it builds trust. So when you come around the next day, you ask somebody to do a task that they really don't want to do. You have this trust built up so they'll be more friendly to doing things that are uncomfortable or burdensome. I think it's all related.

Dan Freehling (00:44:50):

I think that's so right. And they're not feeling like you are out to kind of kiss up and kick down or protect your own area and throw them under the bus for something that you're genuinely looking to solve the problem in the best way possible or explore an opportunity in the best way possible. There's a lot of research on complexity leadership and this idea that when you're moving beyond simple problems like in an industrial era factory kind of a setting where the boss knows the answer already, and it's just how do you get the workers to solve the problem with the least variance possible? And it's instead a startup mentality of, we want to tackle this big challenge together. We don't know the best way to go about that. We're going to figure that out as a team. We're going to overcome obstacles and hurdles and unexpected things along the way and do that together, that this kind of way of leading and way of thinking is really where you need to be focused.

Corey Spitzer (00:45:48):

I would be amiss if I did not caveat this by saying that along with the trust that you build up, then another way you exercise that is to say, great, we've heard everybody's ideas. I am here to make the final judgment call based on my best judgment. And you may go with a direction that may disappoint some people, but because you've had an open forum, because you've talked about your way, how you are approaching and how you're thinking about the problem, and if you actively listen and foster an environment where people can put forth their persuasive arguments, when they're overruled, it goes down so much more easily because not everybody can get their way when you've got two contradictory ideas put forth, and there's a whole facilitation piece to that. How do you hold a brainstorming session and keep everybody on track and focused and discipline so that if it's the type of meeting where you shouldn't negate other ideas, then that doesn't happen. You can hear from everybody, not just the dominant voices. Like I said, everything just interplays with everything else.

Dan Freehling (00:47:07):

It's alright. No, you have such a grasp on the organizational dynamic side of things, which I think is not always the case for executives. But yeah, it's just so important that it's so important to a functioning culture. Let's say I've mixed feelings toward the Amazon culture and all that kind of stuff. They have a disagree and commit concept that I think is really useful for people and it's an important thing. It's exactly what you were saying of you want to foster disagreement and dissension and different ideas and brainstorming and all of that, and then when a decision is made, you and everyone else need to commit to it because it's the best decision for the organization and that's all there is to it. You can't continue the arguments and disagreements after those decisions been made. That's for before,

Corey Spitzer (00:47:54):

And something I learned at my last full-time gig, like I said, I was VP of engineering, I was working with this guy. We worked famously together. I had never laughed so much at a job before with this guy, but I kind of came to a conclusion because we have this pattern where if we had a disagreement about the right thing to do or the right way to go about things, we would always a hundred percent of the time be able to resolve that within 20 minutes. So now when I go to other companies, that's kind of my rule of thumb is can we hash out and come to a resolution of a disagreement in 20 minutes? I feel like that's a really good amount of time. And when everybody's well-intentioned and they're not overly emotionally attached to an idea and they have that mentality of disagreeing commit, then it's totally possible. This is great. I think this needs to be

Dan Freehling (00:48:55):

A new rule that should be named after you in some,

Corey Spitzer (00:49:00):

Well, we called it, well, I informally called it the art of civil disagreement.

Dan Freehling (00:49:06):

Oh, I love,

Corey Spitzer (00:49:06):

I've certainly seen the opposite case and what that looks like.

Dan Freehling (00:49:13):

It's so true that it just throws everyone off their game and the whole staff or whoever is involved in it has to then spend their time politicking rather than getting to the root of something or moving something forward. And it's just such a waste of effort and it slows down that whole flywheel effect of the company that's really humming and moving forward on stuff.

Corey Spitzer (00:49:37):

And I mean, this is something I have to exercise all the time because I'm hopping from company to company and I will give my absolute best advice to somebody to A CEO, let's say, and sometimes oftentimes to the detriment of my income potential. A lot of times people will say, oh, now build this and build this and build this. And I'll have to dissuade 'em and say, well, I kind of think you should start selling what's already built and validate that these other features are actually going to be needed. But if you overrule me and you want me to build more, then I definitely can. Or even if it's not, if it's just, Hey, this is my strongest opinion or strongest recommendation, here are some data points and from my past experience seen this work, and I think you should do this. You just have to live with the fact that it's their company and not harbor any feelings and compartmentalize it. And also, I try to see a way that a conflicting decision might work out, and I just try to continue on in those guardrails, but I don't think any client of mine questions my good intentions that I want the best for them no matter what.

Dan Freehling (00:50:56):

It's such a smart way to persuade and communicate, to lay it out in that way. It allows you to say, with full force, what do you actually think and say, it's up to you and I'll be behind it no matter what the call is here. And I think that's so much more powerful than getting really emotionally attached in one particular way of doing it, and people feeling like they're going to be hurting your feelings or throwing you off or something if they go a different way. It's the way to give really strong consulting advice, I think, as well.

Corey Spitzer (00:51:28):

Yeah, I mean it's easier said than done. You can't really turn off emotions, but especially when you're so sure about something. But I don't know, there are other, there's so many other options, other areas that I get gratification from when I engage with a company or I think anybody, there are lots of ways you can get your endorphins going.

Dan Freehling (00:51:55):

It makes so much sense. And I've heard this concept put as having multiple hierarchies that you're part of. It's kind of a strange way of phrasing it, but this idea that you shouldn't make climbing the ladder at your job, the only thing that's important in your life and just having other interests to your point and other areas where you get satisfaction gratification in life, besides that, it frees you up to not be so concerned with every single little thing in your main job.

Corey Spitzer (00:52:25):

Oh my God, yeah. That reminds me, you just jogged my memory of this concept, what do they call it? The external locust locus of control.

Dan Freehling (00:52:35):

Yeah.

Corey Spitzer (00:52:35):

Yeah, that's it. Yeah. If you pin all of your hopes on this one thing happening that is controlled by another person, that is a recipe for disaster. It's so

Dan Freehling (00:52:49):

True. I just put out a podcast with a really interesting guest, but he had done a lot of work running the streaming service of the World Poker tour before his current role, and he was bringing all these poker lessons into things, but that was a big one, was this idea of you're going to get hands dealt to you, and then you should spend your time deciding how you're going to play it. And then once you've played it, or in the roulette example, once you've decided which numbers to play and then it's out of your hands and you can stop worrying about it, I think it's just a really important broader life and business lesson.

Corey Spitzer (00:53:23):

I think putting your happiness or your goals in the hands of other people to the extent that is possible, to the extent that you can avoid doing that, is the best way to go about things. I know. Yeah, it's tough sometimes when you just have a series of bad luck. You go from job to job, you can't get a promotion, you can't advance or whatnot. But I don't know, somehow I've been lucky enough to rely on other things to always be able to say, well, I didn't get that thing over there. But I think there is, this kind of speaks to the mentality of abundance. I mean, this applies to sales. I could say, I really want to work with that company. I put together the best proposal, and they said, no, we went with somebody else, but there are 300 other potential really great companies to work with. I just need to find them.

Dan Freehling (00:54:20):

It's so important. It really is. It reduces the kind of desperation that really throws people off from a sales process. And just in general too, if people can feel that you really need something to go one particular way, there's going to be so much more resistance to that then if you're coming at it from that grounded, secure place to your previous points. And the abundance mentality too.

Corey Spitzer (00:54:44):

Yeah. Again, easier said than done, but however you can pull it off, please do

Dan Freehling (00:54:51):

So. Right. So which books or other resources of any kind doesn't have to necessarily be books have had the biggest impact on you as a leader?

Corey Spitzer (00:55:00):

That is really tough. I will tell you, I read fairly recently a blog post called How to Help Under Performers. It's by a gentleman named Luca Rossi, and he wrote this amazing blog post of How to Help Under Performers. But it captured, have you ever read a blog post that you may have been able to write if you sat down and could tap perfectly into all of your past experiences and your subconscious, but somebody's done it for you and better than you could do. And in just a beautiful way, that's what this blog post is about. And now it's kind of like it put into a nice framework how I need to think about managing people and addressing issues and things like that. Apart from that, I am very sporadic. I am on certain mailing lists I've kind of just discovered and I'm gorging myself on everything.

(00:56:00):

And there I'll be listening to bits and pieces of different podcasts and always exploring new things. But it is really, personally, it's hard for me to read a book. I don't make time to read paper, but whenever I'm on any kind of trip, say to Lincoln, which is now our way, I will put on a podcast, I'll find the best thing that I can find in the moment. But I will say every month I get together with a couple other people that manage technical people, some technical managers, and we'll trade notes, and we get really insightful, and I should record these sometimes, but they're pretty candid. So it's good to have a support group where you can validate some findings and some patterns you're seeing and maybe get some advice from people who have been in similar situations. So I'm very much a face-to-face kind of person, so I think more so than blogs and podcasts is just commiserating with people.

Dan Freehling (00:57:04):

So we'll definitely link to that blog post. That sounds like a really great read for people on this support group. How did you get involved in that? How did that come about?

Corey Spitzer (00:57:15):

Some years ago, I was managing someone who was being an extraordinary challenge, and I was at a loss, and so I was on this Slack community. It was like a regional technology or startup type slack community. I'm not sure which one it was, but I found a couple people, I just started a private message and I'm like, Hey, would you be interested in a Zoom call maybe once a month? I am dealing with a situation over here. And we started that up. And so basically to answer your question is I just asked and people got busy, it kind of died off, and it died off as another person just heard about it and she wanted to jump in. So I'm like, well, we used to hang out together, but she moved from Omaha to the West coast. So I'm like, well, why don't we just catch up generally and have a monthly call? And it kind of turned into a revived version of this. So now I've brought in a third person, and it's actually the third person is somebody at one of my clients. So we're kind of helping each other out off hours comparing notes and conversations in particular with one client. So it's morphed and changed. But I think the central principle is just as everybody needs mentors, lean on your community and don't suffer in silence.

Dan Freehling (00:58:54):

It's great advice for people and building that professional network and how helpful that can be. So thanks for sharing that, and again, we'll link to the blog post for folks to check that out as well. Corey, just thank you so much for joining me on this episode. I really appreciate it. How can listeners learn more about your work and get in touch if they'd like?

Corey Spitzer (00:59:14):

The best way is on LinkedIn. I'm Corey Spitzer on LinkedIn. Also, my website is flyhighventures.com.

Dan Freehling (00:59:22):

Great. So we'll link to all of those in the show notes, and again, would encourage anyone to check out Corey and reach out if any of the services sound interesting to you. And Corey, thank you so much again, I really appreciate it.

Corey Spitzer (00:59:33):

And if anybody ever is in the Omaha area, hit me up and we'll get together.

Dan Freehling (00:59:38):

Good stuff. Alright, well thank you again, Corey. Appreciate it.

Corey Spitzer (00:59:41):

Thank you.

Dan Freehling (00:59:42):

Hey everyone, I hope you got a ton out of that episode and if you did, if you could please share it with someone who might find it valuable and take a second to leave a quick review on whatever podcast app you're using. Even just the stars is great. It goes a long way in helping others to discover the show. And if you liked this episode, check out our previous episode with Rob Grazioli on Co-Founder Chemistry, billion Dollar Valuations and the Power of Staying Small. Here's a clip from it

Rob Grazioli (01:00:05):

And it's going to suck early on. You're not going to build the perfect thing, you're not going to have the perfect process, but you need to just, the goal is always spend as little money as possible trying to build the right thing, not do it the right way. There's no such thing as the right way and anyone sort of telling you that there's a right way to go about something is almost guaranteed to be wrong. And a lot of those hires are people trying to do that, I think.

Dan Freehling (01:00:32):

What are some signs that you look for in terms of when a business is found fit?

Rob Grazioli (01:00:39):

Revenue, the deal. There's a difference between building something that has utility and building a business, building something that people use and is just simply not a market fit. It might be that you've built something worthwhile or interesting, but you need to have validation that It's something people will pay for or else you don't really, a business, you have a tool that's interesting, but you, you're still figuring out how to have your business. Of course, there are examples that are counter to that where a product goes gangbusters and the sentiment is there's enough users, it's valuable enough, we'll figure out how to be profitable or monetized later. But that is a small percentage of businesses. You need to validate whether or not your business model works as quickly as possible, and the only way to do that is to put payment in front of somebody and tell them to vote with their dollars. In my opinion, that's what we look for, but at our stage it's often premature. So we really try to make sure one founders have that mindset, and two, try as best we can to validate that there's real potential there. And also give founders the structure to experiment with pricing and actually capturing revenue early.