As a business owner, it’s difficult to do the right work AND guide your company toward its next big initiative.
With Red Direction Business Base Camp, learn how to implement and handle processes to meet your business’s specific needs and better understand your market.
Starting the conversation:
There are invisible signals separating bold business moves from costly missteps. Calculated risk, financial, emotional, and business, is what unlocks opportunity. Scott Kelly, CEO at Black Dog Venture Partners, shares how to survive mistakes by listening for your next big clue.
Rapid change is normal for a modern business to embrace, and AI requires entrepreneurs to evolve their business strategies. Start with what you know: strengths. The strengths of your business, you, and your partners. Then look at the way AI is shaping your industry and the changing needs of your customers (and how they buy).
In this episode you will hear how to find the clues to success or failure; apply effort to getting good at what you know so that it is clear when you don’t know; and identify what results indicate success because business success isn’t defined by the same path that it used to be. That adage “don’t judge a book by its cover” is more important today than ever before. Jess Dewell talks with Scott Kelly, CEO at Black Dog Venture Partners, about being BOLD and committing to big moves.
Host: Jess Dewell
Guest: Scott Kelly
What You Will Hear:
08:30 Recognize growth limits and pivot as needed.
- Know when you’ve reached your learning potential in a role.
- Know what will prompt him to consider new opportunities for employment, business partners, and businesses to start.
13:10 Entrepreneurs, put attention on finding — and admitting — when you are on the right journey.
- Entrepreneurship requires a willingness to deviate and create your own way.
- Having an idea is not enough — success comes from the execution and perseverance to bring it to life.
- Stay engaged on multiple levels — mentally, emotionally, and socially.
20:30 What does it take to know your strengths — and hire for your gaps?
- It’s essential for founders to recognize the limits of their expertise and seek out complementary skills in others.
- Investors look for well-rounded teams, not just solo founders, so bringing in experts early increases the chances for success.
- Surrounding yourself with people who are strong where you are weak is critical for growth.
27:10 What do failure and timing mean for growth and innovation?
- Market timing can make or break an idea — sometimes great concepts fail because they arrive before the world is ready.
- Mistakes are valuable learning opportunities if you adjust your approach afterward.
- Unsuccessful ventures provide experience and wisdom that guide better decisions in the future.
34:25 How is AI changing the landscape for entrepreneurs and investors?
- AI is helping businesses operate more efficiently, get products to market faster, and reduce costs.
- Investors now have advanced tools to evaluate more opportunities quickly and make smarter decisions.
- The speed of change in business driven by AI means both entrepreneurs and investors must constantly adapt their expectations and approaches.
39:25 It is BOLD to commit to do what it takes to make the impact you desire.
Resources
Transcript
Scott Kelly 00:00
At the end of my meeting, he gives me a check for two million dollars and I think it’s my second, maybe third day in the business, so I said, Mr. Hebert, I don’t want to be rude, but how did you get this money? And he walked me to the side of his house and what used to be rice fields was oil derricks as far as the eye could see. Mr. Hebert was making eight million dollars a month in oil royalties. If I would have drove up, looked at the house and kept driving, I would have missed that opportunity.
Jess Dewell 00:27
By the way, that is like the best story ever.
Announcer 0 0:37
Every leader needs a trusted partner for the moments that matter. This bold business podcast conversation is that partnership, your go-to resource designed to break the inertia and refresh your perspective so you can start making moves. Here is your host, an insightful truth teller who serves as the catalyst for getting the right work done and who asks the questions that truly matter, Jess Dewell.
Jess Dewell 01:03
We all have ideas of scaling and sustaining innovation. Scott Kelly, the CEO of Business Accelerator Black Dog Venture Partners and founder of VC Fastpitch has been on both sides of that equation, the building and scaling and the investing of those building and scaling. For over 30 years, that’s three decades, yeah, 30 years, he’s been taking his innovative skills and all of the experience that he has been building and he’s trained thousands of salespeople and mentored as many entrepreneurs.
His network is vast and he wants to help founders and investors scale and innovate and ultimately succeed. How he does that is very interesting. I’m going to start you out with these three things to listen for.
The first is that our growth journey is ours. It’s ours to find and the clues are there. Will you listen?
The second is that it’s really important to know what we’re good at and get very familiar with it so we know what we’re not good at too. The third thing is there’s always changes to the way we do business and it’s quicker than ever before. Recognize and harness exactly what is needed today for you, for your industry so that you can achieve the most success with being intentional for your own success.
I can’t wait for you to hear the whole conversation. Let’s get to it. I want to know, did you know what you wanted to be when you grew up?
Scott Kelly 02:45
It’s interesting you say that. I started my entrepreneurial journey when I was 11 and basically what I was doing then, I did all the traditional things, set up a lemonade stand and some other things, but then I built a pretty lucrative business in trading cards, baseball cards. Basically, I would buy them in bulk and sell them to my friends.
I knew then I wasn’t set to be an employee. I tell everybody, I think I would work for somebody else. I think my entire career, maybe 18 months, and I tell people that’s because I’m a bad employee.
I’m a good employer, but a bad employee. I learned pretty young. That’s where I was going.
Jess Dewell 03:23
What are the elements of a good employer?
Scott Kelly 03:26
Flexibility, compassion, the ability to lead, the desire to coach. Those are the attributes of a successful career.
Jess Dewell 03:39
What are the attributes of a bad employer?
Scott Kelly 03:42
I believe I like to empower employees. I think that is a really bad thing for employers to do is micromanage people. You have to hire slowly, fire quickly.
When you’re hiring slowly, you need to make sure that they have all the tools they need to be successful and you give them the power to be successful because the reality is if you give someone responsibility without authority, it becomes anarchy in my opinion.
Jess Dewell 04:08
Fair. It becomes real risk and anarchy, I think is one of those most common outcomes, isn’t it?
Scott Kelly 04:13
Yeah, absolutely.
Jess Dewell 04:15
Yeah, for sure. I find that interesting because you also work in a place where you do VC funding. People want this so they can scale and grow and hire fast.
Those are the polar opposites of each other. Explain that to me.
Scott Kelly 04:28
The reality is that companies of all sizes at some point come to an impasse where they might be able to sell their way through their financing, but then some of them have to find financing, whether that be debt or grants. I work really on the equity side of the business. The reality is that the large use of the proceeds of a lot of companies is to hire more staff.
If you’re an investor investing in a company, you need to make sure that they’re hiring the right staff because if they don’t, you get turnover, you get bad results, and that leads to underperforming investment for the investor.
Jess Dewell 05:06
I was going to say, wasted money. Absolutely. Do you actually say that to people?
Scott Kelly 05:13
I have. Yes.
Jess Dewell 05:17
I’m thinking about what’s funny in our household. We come from a technology realm and a background, and my husband is a technologist. He is rewatching one of his favorite shows, Halt and Catch Fire.
There are some parts that are very real. There are parts that we have experienced. There are parts that are very harsh, yet even though they’re harsh, I’m going to go back to the compassion piece.
In the moment, they felt harsh for the sake of being harsh and failure, but looking back and that reflection piece, there’s actually a lot of compassion in there. Can you tell me a time when you’ve thought about, how do I say this compassionately? Is there a way?
Can they receive it this way? That two-way street of communication that maybe doesn’t always come through.
Scott Kelly 06:02
Obviously, I’ve had to hire and fire hundreds of employees and staff and consultants in my career. I’ve tried and, for the most part, been successful in terminating relationships positively. What I mean by that is that obviously, I think a lot of times both sides come to the conclusion that it’s not working out.
One of them has to act on that conclusion. When I do it, it’s, look, if this is not a right fit for me, but it is a right fit for somebody else, let me help you find that somebody else. Obviously, in addition to giving them some recommendations and advice, we want to turn a positive because I’ve had instances where, quite frankly, there are employees I had to let go, but I maintained the friendship and the relationship.
Then it became very successful and quite frankly, they became clients or partners afterwards. It just wasn’t, sometimes it’s the personality fit, sometimes they’re not suited for the job. I started out as a programming major, that lasted a semester.
I spent another semester as an accounting major, realized those two things weren’t me and I’m getting my degree in marketing and finance. I had to find my way to the thing I was best at. A lot of times, that’s what most people have to learn.
Jess Dewell 07:25
Who told you, who gave you one of those harsh truths and did you take it, it was actually compassionate?
Scott Kelly 07:32
Yeah, I did. Honestly, I have never been fired from a job. I quit several jobs.
I remember one point I started out as a stockbroker and I had a very successful career with this firm for a couple of years. I remember one day out of their several hundred representatives, I was the number one producer for the week. I broke every record by fivefold.
Then the CEO decided to host a party at the other office for the firm’s record week. I go, wasn’t I pretty much all of the record? That was a little disheartening.
Fast forward, I realized very soon after that I was making three, my commissions were three times the CEO’s salary. I really came to the conclusion, okay, this is, I need to be somewhere where I can really grow. That was really where I came to the conclusion, I was a bad employee and decided to become my own boss and run my own company.
Jess Dewell 08:31
So you were actually feeling, were you actually feeling the upper limit of growth in that organization?
Scott Kelly 08:37
Yeah. I think what I found in my early years in sales is they take the best sales people and they put them into middle management. And so they take a pay cut and they take away the real skills that they have and replace them with skills they don’t want to use.
That was happening to me.
Jess Dewell 08:53
I think that’s very true. There are some people and I’m one of those, right? It sounds like you’re a fixer in your own right.
It could be a starter, a new idea. It could be a shake it up, tear down and rebuild. There are all kinds of things that fall into that category of, there’s this thing that does really well for me that brings me joy.
And how do I use this? What I find interesting is even today with all the technology advances, I’m finding there’s still this push of, you gotta get a job. You gotta have a skill.
You gotta do this thing. And you and I are examples of the opposite of that. By the way, I’m watching and I’m thinking, and I fight this as a parent, you gotta get a job.
Your grades gotta get you to the next level. And I have to step back on a regular basis, which by the way, changes the way that I also, I wish I had learned, I wish I’m a parent less long than I am a business owner. So I wished I’d learned this lesson before I had a child because it works in business too, of how can I show up and make sure that I’m not accidentally bringing a, an untruth or something I don’t actually believe into the way we do our work.
Have you ever had to face that in your, for yourself?
Scott Kelly 10:08
Yeah, obviously I have, I have two boys, one’s out of college and has successful business on his own. The other is a senior in college. And I tried to tell them at the beginning, you may go in with one idea of what you want to do.
It’s going to change multiple times. And one thing I learned with my two boys, and I tell everybody is that as a father from 15 to 25, nothing. And then my son turned, my oldest son turned 25 last year.
It was like an epiphany. All the things I tried to tell him advice-wise, all of a sudden he believed. And, but I still have one son in the cone of doubt.
And so I, that’s obviously, that’s something I learned from being a father. A lot of those things apply in business. I work with entrepreneurs all the time that get tunnel vision.
They think their idea is the right idea. They’re the right person to handle everything. And they soon learn that’s not the case.
It’s again, getting back to my sons. I can tell them not to touch the poison ivy. They will stop touching poison ivy once they touch it once.
Jess Dewell 11:08
I can tell you live in a, actually, I love that. I know that people tend to use the stove idea, but let’s just be real. We’re an adventurous family too.
And I might have to use your analogy of poison ivy because it’s way more applicable to the way we live and the hobbies that we have as well. What are some of your hobbies?
Scott Kelly 11:24
I live right on the water. So I kayak. I just began kite surfing, a little bit of Tai Chi.
I’m a workaholic. I love what I do. I tell people I’ve unsuccessfully retired twice in my life.
So I really have a passion for what I do. And that takes a lot of my time. I travel quite a bit.
My fiance and I are going on a cruise in a couple of weeks. We go to a lot of concerts, those kinds of things I like to do.
Jess Dewell 11:46
What kind of concerts?
Scott Kelly 11:47
Quite frankly, many of them. We’re actually going to go see Stevie Nicks in December. We were scheduled to see Billy Joel, but he got sick, unfortunately.
We’ve been to a lot of, I’m in St. Petersburg, Florida, which is a really good downtown music town. So there’s a lot of local bands, jazz bands, and reggae bands that we like. But ironically enough, I actually can’t play a lick of music, but I invested in a record label and got a gold record.
So I try to use my business to motivate my hobbies and vice versa.
Jess Dewell 12:17
Stevie Nicks, was she part of Heart?
Scott Kelly 12:20
No, she was, you caught me here. It is my fiance’s favorite artist. Honestly, you’re going to have to edit this out and AI the name.
I just don’t know.
Jess Dewell 12:29
We’re going to do a quick Google search. This is not something we usually do in our conversations. Okay.
Cause I’m like, hang on, I got this wrong. Okay. So Stevie Nicks.
Okay. So let’s just look and see. Fleetwood Mac.
Sometimes we’re focused on other things and we cannot recall as fast as you. So thank you for playing along. I only have one child.
He’s 14 going on 30. So he’s right on each side of your, you called it the cone of doubt, which I love because I went, Ooh, I know where that is in business. Oh yeah.
So here we go. And I think that’s really interesting because how many people out there do you actually think take the time to find their right journey?
Scott Kelly 13:13
It’s interesting you say that, because I think that the makeup of someone being an entrepreneur is unique. I think like you mentioned before, a lot of people just go through the motions, go to school, get a job, retire or leave and go to another job in the same industry. I think being an entrepreneur is for me, one of the greatest things you get to do, but it’s also one of the biggest challenges because having a great idea is wonderful.
Being able to execute on it is the real superpower. And I think that’s the challenge that a lot of us have out there. She has a great job working for a great company, but she is not inspired.
She’s not impassioned. And for me, I have to be, I have to be mentally, emotionally, and socially entertained. And I do that by being an entrepreneur.
Jess Dewell 14:05
I understand everything that’s in front of me is my favorite thing. And the next thing will be my favorite thing. And that’s actually something that people told me, you got to remember all of this stuff.
And I’m like, why? I want to be really present right now. I can capitalize on this.
And I don’t know if that really makes a good entrepreneur or not. It sure does make great conversation. And that through that conversation, learning, risk, exploration of ideas.
And usually, even though there’s a lot of good ideas that are probably good enough, there’s usually one or two in there that are the right thing to take to someplace else, whether it’s share with another company, whether it’s give in a mentoring situation, whether it is conversation over dinner, whether it is, I hadn’t thought about it that way. What if I listen today through a new lens? And I think that those, all of those things are what come of my being super present.
What’s your superpower?
Scott Kelly 15:04
I think my superpower is my ability to multitask and to come up with ideas and conceptualize them quickly. You know, I’ve launched several companies on my own and I work with a dozen companies simultaneously. I think my superpower is I’m very efficient about how I get things done.
I’m a very quick study because I am a relatively good speaker and a pretty good salesman. I’m able to move quickly and work on the fly and talk on the fly. I tell people when I was a kid, I was good at doing two things, getting into trouble and getting out of trouble.
And I apply those same things to my, my, my career in entrepreneurism.
Jess Dewell 15:44
I think your superpower is getting into trouble and being able to get out of that same trouble because doesn’t every little bit of trouble come from a good, a good quote-unquote idea.
Scott Kelly 15:53
I’m in the idea business and the vast majority ideas are, I get probably two, 300 pitch decks in my inbox every month. There’s probably two or three that hit my LinkedIn while we’re on this call. And the reality is there’s a lot of good ideas, but there’s a lot of bad ideas.
And the difference is knowing what they are quickly.
Announcer 16:21
Feeling stuck, like what got you here? Won’t get you there. The pressure to grow is on, yet the path isn’t clear yet.
You don’t have to walk that path alone. This is the bold business podcast, like, and subscribe wherever you listen. Your host, Jess Dewell, is the strategic partner you’ve been looking for asking the questions that truly matter.
It’s time to break the inertia and get the perspective you need to make your next move.
Jess Dewell 16:55
I’m really excited to be talking with Scott Kelly, the CEO of Black Dog Venture Partners. And we’re going to get back to the show. What is a good idea quickly versus the bad ideas that might be okay, but not the idea?
Scott Kelly 17:08
I think a lot of it is I have being around for many years and doing this. I have two things primarily experience and perspective. You know, I have made and lost millions of dollars myself on good ideas and bad ideas.
So I can speak to that to the companies that we work with or invest in. I think the other thing is that I try to have a relationship where it’s open communication. And I like the entrepreneurs I work with that tell me the good news and tell me the bad news.
You know, it’s like my kids, they’re both very good students and they’re well-behaved kids. Every once in a while they come home and I know they did something wrong. And you might as well just tell me, because I will find out and the same applies in business.
You can hide for only a short period of time when you make a bad decision.
Jess Dewell 17:59
True that. And okay. Oh, I have so many places I want to go.
Scott, let’s see. I’m thinking about emotions because we’re talking about being able to discern. We’re talking about good ideas and bad ideas.
We actually, we’re talking a lot about compassion too, right? Some of these skill sets that are here. How about if we start with, I feel like emotion belongs in here.
I’m not sure about you. I know from my perspective and my journey, I have carried a lot of guilt. I have carried a lot of shame and embarrassment in times that it was warranted, but most often not.
I was taking on these things in the wrong way. I still find myself doing that sometimes. Oh, I could have done that.
Oh, I wish I had seen that. Oh, the clue was there and I fill in the blank about it. So I’m curious, do you still have emotions like that too in the decisions that you’ve made and the way that you’re working?
Or is there this point where it doesn’t matter anymore?
Scott Kelly 18:52
Yeah. At this point in my life and career, I don’t have a lot of fear about the business side. Obviously I fear for the safety of my kids and I fear for the safety of my fiance and my good friends and my family members.
But when it comes to business, I’ve learned if you build it right and you veer, you can move it back to center very easy. I don’t necessarily have a lot of fears from that. And I think a lot of entrepreneurs have fear from just not knowing.
Jess Dewell 19:21
Yeah. There’s a lot of that. Yeah.
Scott Kelly 19:22
Yeah. Being an entrepreneur for the first time is the great unknown. And I tell people, look, you’re not going to know a lot of the mistakes until you actually make them.
And that’s just unfortunate, but that’s just the fact. And I’m in the risk business. I tell people that venture capital and baseball are very much the same.
If you get back 300 in either, you’re in the hall of fame. And so there’s risk involved and risk can invoke fear.
Jess Dewell 19:49
It can. And that’s one of the ways to work with that and to learn from it. I’m going to call it leverage because we can use fear as a propellant, as a motivator, pause to look a little closer, whatever it is, right.
There’s all kinds of ways that we can use that. So I’m thinking about things that we don’t know what we don’t know, especially if we’re anywhere in this cone of doubt where we think we know it all, but we really don’t. So people looking at us go, okay, we got you.
And they have been there. Like you have been there and can say, okay, I see where you’re at. What are the things that you guide and say, Hey, this is actually what you can influence.
This is actually what’s in your control, which is not a lot.
Scott Kelly 20:31
I work with a lot of entrepreneurs and they typically start off with a single founder. Maybe they’re a technical founder and they’re a good programmer, a good designer. And I tell them to do two things.
First, get a real good understanding of what you know, but then also get a really good understanding of what you don’t know and fill those gaps with people that you know and trust because as an investor, they want a team that they’re going to invest in. So if you are a programmer developer, but you don’t have accounting skills or marketing skills or organizational skills, you can try to do it yourself. And a lot of entrepreneurs do to a period of time, but at some point bring in the experts in those categories.
So you can focus on being the expert in yours. And I start with that with a lot of entrepreneurs because a lot of them started as solopreneurs. As soon as you start to want to raise money, investors are going to ask you, who is your team?
And they’re not interested in a team of one. And I think those, that’s the early pieces of advice I give entrepreneurs. Surround yourself with people smarter than yourself in areas that you’re not smart at all in.
Jess Dewell 21:38
And develop really good relationships.
Scott Kelly 21:39
Absolutely.
Jess Dewell 21:40
Understand where are the triggers in them? What makes you so angry that they do? What do you do that makes them angry?
Not because you have to change, but because that’s how you know, you work dynamically. If I’m under pressure, I’m going to act a certain way. If you know that about me and you see that pressure coming, you can meet me where I’m at from your expertise in your lane.
So we can stay hooked together by the arms to keep moving forward. And I think that it’s easy to say, surround yourself with smart people. And it’s easy to say, have good relationship that only comes by getting in the mud together.
Scott Kelly 22:12
I agree. I tell entrepreneurs, especially when they’re out there trying to find investors for their startup, they ask me, when should I begin to make contact with investors? I tell them six months before they need it.
You’ve got to build relationships because people do business with people they know and people they like. And so what you want to do is get to know a lot of people and try to get enough of them to like you. And I think that’s where the relationships come in.
And because the reality is when you’re, someone was so desperate to bring in an investor, they brought in a bad investor. Someone who didn’t have the same personality, the same agenda, didn’t match from a personality standpoint, and it was a disaster. And I tell entrepreneurs all the time, do your homework on them also, because in most cases, if not all, a bad investor is worse than no investor.
Jess Dewell 23:04
Was there ever an idea that you were like, nope for me and somebody else got it and it turned into something crazy awesome?
Scott Kelly 23:13
Yes.
Jess Dewell 23:14
Can you share one or is that, no, you don’t want to share.
Scott Kelly 23:16
Wow. I see so many deals. I don’t know which ones to pick.
And I had an opportunity to invest in Google and I passed. And obviously, that was a less than intelligent decision. And so again, it’s happened many times because, obviously, sometimes a good idea may not be a good idea today, but it could be a good idea tomorrow.
And there are many examples of that.
Jess Dewell 23:42
I think that’s such a key thing to say and to be, to have be part of this conversation, because I know one of the things I work with is how do you prevent competing priorities? And how do you ensure that you’re doing the right thing right now? Because all of these things are possible, but if they’re not aligned, let it go.
And so be it. So being able to say, hey, I could have done that. And I didn’t all that and not having as much fear about the business side of things.
It’ll work out or alone to your point. If you’re batting 300, here you go. You’re winning.
Yeah. Okay. All right.
Now, so you, do you have a high tolerance for risk?
Scott Kelly 24:21
Yeah. You have to in my business. Absolutely.
Jess Dewell 24:24
So you have a high tolerance for money risk.
Scott Kelly 24:26
I have high tolerance for a lot of risk. I’ve done a lot of risky things in my life. When I got out of grad school, I’ve done a lot of risky things in my life.
I’ve broken some bones. I’ve gotten some trouble in some other countries because I just took risk. I think sometimes I’m a firm believer.
You got one shot at this. You might as well make it interesting.
Jess Dewell 24:48
Yeah. I think that is fantastic. And so you said you’re good at getting out of trouble too.
Have you ever gotten into a place that it took longer than you wanted it to? Or was there any time it was like, I actually did not get all the way out of that one.
Scott Kelly 25:02
Oh yeah. A couple of times on the investment side, I got involved in some companies which were famous for their failure and I decided to stick it out longer than I should have. Back in the nineties, I was very active in the internet boom and had some very good success during that time.
The reality is I stuck my neck out on a few that I probably shouldn’t have believed and things that I shouldn’t have. And sometimes you let the rose colored glasses apply in investment and entrepreneurism as much as anything else. So yeah, absolutely.
That’s happened.
Jess Dewell 25:33
And you know, we can have all the right people and we can have the right idea and it can still be the wrong time.
Scott Kelly 25:38
Absolutely. And there’s great examples of that. I remember during the nineties, two of these tremendous early ideas, one was pets.com and the other was a company called Webvan.
Jess Dewell 25:49
No way. I remember them. Okay.
Scott Kelly 25:52
And both of them were colossal failures because they were too early. Now, today you have Chewy and all other places to buy pet products. And I just got a delivery from Walmart, my food and another delivery from another store of my food.
They both existed. Webvan, they ended up with the only thing left was the sock puppet and with pets.com and Webvan spent well over a billion dollars and lost it in record time. So again, great ideas need to be aligned with great timing.
Jess Dewell 26:25
Yeah. And I think that might be something for anybody who’s listening right now that is disheartened or coming off of something is, Hey, if it’s the right thing, the conversations will keep coming back to you. So don’t give up on it.
Also don’t put all your eggs in that basket because the right, it feels like it emerges. In my experience, the failures that I’ve had, there were clues there. I should have listened there.
There’s a lot of shouldas on that. And at the same point in time, I’m like, if I were to do it again, I’d probably, if I were to do it today with this knowledge that I have today, I would never have done it. However, in that moment, it would have taken some other weird things to play out unexpectedly for me to actually see the clues.
And that’s an okay thing because that’s how we learn. That’s how we get our own wisdom.
Scott Kelly 27:12
You have to fail forward. You have to take the things that you’ve made mistakes on and use them to be better the next time around. Both of my sons played sports and I told them, look, if you missed that play, figure out why you missed that play and don’t do it again.
Jess Dewell 27:28
Right. What sports did your boys play?
Scott Kelly 27:32
My boys play basketball. My younger son played football and lacrosse.
Jess Dewell 27:37
Yeah. Okay. I think lacrosse is a very interesting sport and I love how popular it is becoming, but I’ve never actually watched a game and I don’t think I know any of the rules.
It doesn’t mean I wouldn’t like it, but, and by the way, can you do that in business? Can you join with not knowing any of the rules or how to play?
Scott Kelly 27:53
That’s being an entrepreneur, quite frankly, is breaking the rules. The reality is I tell people, like I said, the reason I’m not an employee because I’m not a rule follower. I’m a rule creator and I’m a way, and I know ways to, my good job is to get around the rules or in a proper way.
But sometimes if the speed limit’s 35, I’m going 42.
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Jess Dewell 28:46
Scott Kelly, CEO of Black Dog Venture Partners, has so much to share. Let’s hear what else he has to say. This is one of my biggest pet peeves.
Tell me how this ranks up in your peeve list. When people come to me and say, I haven’t found a process to do that yet. I’m like, duh, do it.
Make your own.
Scott Kelly 29:06
Yeah. I think the reality sometimes there, I think sometimes that comes up with not just business, but in life and relationships is, if someone wants someone else to solve the problem, that’s the kind of response they’re going to give.
Jess Dewell 29:18
Yes.
Scott Kelly 29:19
And I say, look, we have people all the time, entrepreneurs I work with come to us and say, look, we don’t know how to solve this problem and go back and come back again and go back again. Because the reality is you’re going to learn more by doing it and solving it yourself than having someone else tell you what the problem is, what the solution is. I can tell my kids how to study better, but the reality is a bad grade is going to teach them how to study better.
Jess Dewell 29:46
Cheers to that. Because I find myself going, maybe you should follow this path or asking the questions and shaping something, even though I didn’t do it. Even though my whole experience is not that, that mainstream norm.
What’d you do to get here? Whose path did you follow? Nobody, but your own.
You might’ve grabbed a tip here or a short process there, but how much did you actually grab that you’re still using today in terms of how to do it? The answer is never.
Scott Kelly 30:13
I think it’s important, but also I think you do need to be a sponge with successful people and smart people. I’ve learned from some great people in my career. I’m a big believer.
I don’t judge a book by its cover.
Jess Dewell 30:26
Never.
Scott Kelly 30:27
One of my favorite books of all time was called The Millionaire Next Door.
Jess Dewell 30:31
I love The Millionaire Next Door.
Scott Kelly 30:33
Yeah. George Daly and I were friends for a while while I was at Georgia State. And honestly, it happened in my real life experience.
It happened to me. My very first day on the job after college, I went from New York to Lafayette, Louisiana to be a stockbroker. And I get Mr. Hebert on the telephone. He buys $500,000 on an investment. Meanwhile, this is my second day. I’m 22 years and change.
And my boss goes, look, go out there and pick up that check. And so I go out to Mr. Hebert’s house to pick up that check. And it is a metal shack.
He is sitting on a rocking chair with seven teeth in his mouth. And he’s whittling wood. At the end of my meeting, he gives me a check for $2 million.
And again, I think it’s my second, maybe third day in the business. I said, Mr. Hebert, I don’t want to be rude, but how did you get this money? And he walked me to the side of his house.
And what used to be rice fields was oil derricks as far as the eye could see. Mr. Hebert was making $8 million a month in oil royalties. If I would have drove up, looked at the house and kept driving, I would have missed that opportunity.
And he ended up becoming a phenomenal client and backed one of my companies several years later.
Jess Dewell 31:44
And I think, I love that. And I agree with you about not judging a book by its cover. Are you an avid reader?
Scott Kelly 31:50
I read a fair amount, not as much as I would like.
Jess Dewell 31:52
Or consume, I guess.
Scott Kelly 31:54
Yeah, I’m a constant consumer of information. Yes.
Jess Dewell 31:57
Me too. I like a good TV show and a good movie, but I read or listen and consume what people and their expertise way more than I do anything else. And I think that’s what makes me feel comfortable going, okay, there’s a lot of ways to get to that.
I just have to pick the one that might work for me right now because they’ve got the information. They can be the spark and here we go. By the way, that is like the best story ever.
I was not expecting that to be the outcome of the story. And what a lesson to learn and knowing that he still chose to just sit on his porch and whittle wood. That’s probably what he did on the days he wasn’t working in his rice fields.
Scott Kelly 32:37
I found early in my career, fortunately, that the people that have true wealth aren’t the people that are driving around in Maseratis and wearing Armani suits. Yes.
Jess Dewell 32:51
Okay. So tell me, what are one of your values that you make decisions by, that you show up by, that you learn by, that you seek out?
Scott Kelly 32:58
My father really was a good businessman, a good salesman. He really harped on me. Probably one of the most important things is 15 minutes early is on time.
On time is late. Anything after is unacceptable. And I would go to meetings a half an hour early, sit in my car so I would not be late.
I find that’s important. I think that respects people’s time and it shows that you care. I’m a big believer in under-promising and over-delivery.
In every engagement, I know what I’m going to do. I don’t tell them everything. I let them be pleasantly surprised.
And I think those are things. And be a man or woman of your word. Those are things that are important to me.
I tell people I’m an A-type personality. I’m a New Yorker. I move fast.
And I tell them that ahead of time. I go, look, if we hit the go button, it’s go. I’m going to go.
So you can decide to be in the front seat, the back seat, or the side of the road. Those are the beliefs I have. And that’s what’s led my business life.
Jess Dewell 34:03
Okay. That’s great. And all I can think of now that you said that was, roads, where we’re going, we don’t need no roads.
That’s quoted daily in my life. Speaking of we don’t need no roads, what do you think of all this stuff with AI? And what do you see the potential being for what we don’t even know is coming?
Scott Kelly 34:24
Obviously, it’s a transformational technology. Someone asked me a while back, is AI the equivalent of the internet? I told them, no, AI is the equivalent of electricity.
It is transformational. And in my line of work, from both sides of it, entrepreneurs now, especially tech entrepreneurs, can build their businesses differently, more efficiently, and with less money. Investors can use AI to do better due diligence, to look at more opportunities and make better decisions.
Again, it’s like any tool, you have to apply it correctly. A hammer is a great tool when it hits a nail. It’s a less great tool when it hits your thumb.
And I think the reality is it’s like any tool, it’s going to be transformational. And I think we are in an interesting time. I was there during the internet boom and the internet bust.
We are, there’ll be a bust in AI with some companies who quite frankly just decide that putting an AI wrapper on a bad idea still makes it a bad idea.
Jess Dewell 35:27
That’s how it’s the same as the internet.
Scott Kelly 35:29
Yeah, agreed.
Jess Dewell 35:30
Right? Do you agree with the electricity comparison? And then all of us, it’s going to have that.
And I think it’s going to be faster. Do you think it’s going to be a faster to the bust?
Scott Kelly 35:41
It’s already faster. It’s already faster. I heard recently it’s every seven days.
It’s insane. Because AI, just the computational power is insane. But again, I think it’s going to be transformational.
It already is in some cases, but now for the entrepreneurs listening, they got to learn how to apply that and use it most effectively.
Jess Dewell 36:03
And I think you touched on that when you said that it’s going to change the way that we do business. Now, taking that to the next piece is what I’m watching in disruption from the outside looking in across industries. And I can’t wait to hear what your experience is here too, is that it doesn’t matter about technology.
If you’re on the front or if you’re at the top of the curve, if you’re one of the lagging people, okay, fine, whatever, that’s fine. But our expectations, the intentionality needed. So when it’s time to go get some funding, whatever funding is, that’s going to look like.
And in your case, it would be the VC side, right? There is going, the expectation of what you have done can do with what you already have is changing. And so that is a place where if we think it’s the same way it was the last time we even did our last pitch for our last idea, we could be doing ourselves a disservice.
Scott Kelly 36:56
Absolutely. I had to have a couple of disheartening conversations with some entrepreneurs that didn’t understand the new norm. This entrepreneur came to me, he wanted to build a software product, and he told me that he needed $5 million and 18 to 24 months to build an MVP.
And they go, no, you don’t. You need maybe $10,000, someone who can program the agents and the vibe coders and put together an MVP and actually put together a product where you can sell. And I think entrepreneurs have to realize that now.
They have to realize that investors now have an expectation that you can get to product market fit. You can get to a viable product. You can sell much faster with far less money and it’s happening every single day.
And I think especially tech entrepreneurs really have to understand the new norm.
Jess Dewell 37:51
So do you think we’ll ever fully move away from investing in an idea? Like you have to have the MVP in some capacity.
Scott Kelly 37:58
Okay. That’s good. Obviously there’s some industries where it’s again, changing, but the idea stays, obviously you’ve got industries like pharmacy and biotech and other things that do have an approval process and do take more time.
And again, I don’t necessarily think MVP is a dirty word, but the reality is a lot of entrepreneurs now should be able to build something that they can put in front of potential customers and at least get feedback. That’s important.
Jess Dewell 38:29
Does it help you as a VC investor to see that path laid out?
Scott Kelly 38:35
Oh, absolutely. Entrepreneurs we talk to on a daily basis, when they are trying to pitch or share their vision and mission with myself or investors, they have to have a clear path of how to get from point A to point B. I tell a lot of entrepreneurs start with the end in mind, because that’s where the investors are looking at.
They probably care somewhat about what you’re building and who you’re building it for, their primary interest in the end and how they can get a return of their money and a return on their money. And you have to start with that mindset when you talk to investors.
Jess Dewell 39:10
It’s perfect because the investors, this is a tool to help them with their goals. And this is a tool for the business to reach their goals and they don’t have to be on the same path. They just have to cross.
I want to know what makes it bold? What makes it bold to be intentional about knowing yourself to be able to create your own success?
Scott Kelly 39:32
I think when you’re bold, lean into your strengths. Become even better at your strengths and don’t be bold about what you don’t know. We have conversations all the time with entrepreneurs.
They are intimidated to tell you something they don’t know. And I’d rather have someone to see bold and go, you know what, that’s a really good question. I don’t know.
Let me go find out. And you’ve got to be bold about trying new things. You got to be bold about getting kicked in the teeth and keep moving.
Entrepreneurs fail at a rapid rate. An entrepreneur that started today, the likelihood they could be in business two years from now is very small with or without funding. So you have to be bold because bold gets you up in the morning.
Bold makes you do something you don’t want to do. Tomorrow morning, the leg will work and you’ll work out tomorrow because you’re bold. And I think that’s what bold is when it comes to entrepreneurship.
Announcer 40:39
And that brings us to the close of another powerful and fresh perspective on the Bold Business Podcast. In today’s volatile landscape, growth is a double-edged sword. To truly thrive, you must engage with your strategy, not just react to the day-to-day.
Without absolute alignment, your company faces a stark choice, outmaneuver or be outmaneuvered, grow or get left behind. Thank you for listening. And a special thanks to the Scott Treatment for technical production.