Reinventing The Pitch To Fund Your Business

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All right. Welcome back to The Daily Mastermind! George Wright III with your daily dose of inspiration, motivation, and education.

And I'm joined by what is sure to be an amazingly fun interview with Kent Richardson. How are you doing, brother?

Doing great. I'm excited to be here.

Listen, man, I'm glad our calendars finally synced up because you’re a man on a mission, and you've got a lot of travel on your schedule.

Let me give you a quick introduction for those of you that don’t know. For those listeners that do not know you, Kent's an entrepreneur, investor, and connector. He’s the founder and host of Sht Pitch, like CNBC, which is an investor-focused live pitch event. We’ll get into that in a little bit here, but definitely a man of many talents, tons of skills. I've been really getting to know him and his company a little bit here recently.*

So with that said, Kent, why don’t you give us a little bit of an idea of where you come from? Because we’ve got some cool stuff to cover here today for entrepreneurs and business owners. What’s your background, man?

Give us a little bit of the leading up to behind the scenes of how you grew up.

Gosh, I like long walks on the beach… How far back do you want me to go? I was wheeling and dealing back in grade school. I was the reason we had Pokémon even revoked from the whole school front.

So how far back do you want me to play this game, bro?

What’s interesting is I usually start with a question like, "Were you always an entrepreneur?" But I know that back to when you were old enough to talk, you probably were. Just go back and give me an idea of what’s been your career background.

And were you always an entrepreneur, or did that kind of evolve through just things you were doing growing up?

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Kent's Entrepreneurial Journey

It definitely evolved. I, just like anybody else, jumped into the job space. Most of it, though, has been circled around fractional work—a lot of fractional IT companies, fractional CFO, fractional administration with fund administration, and SPV creation.

So a lot of it has revolved around that entrepreneurial mindset of, “Okay, let’s figure out what is going to work best for you and your needs,” as opposed to the check-in, check-out kind of behavior. A lot of it is circled around that mentality of discovery and understanding.

Fractional is a really big thing right now. But were you into a certain niche of business? Was it primarily IT, fractional IT work, or what other things? Because, look, you’re a sales, marketing, entrepreneur overall, but what area of fractions were you in heavily before you started to get out on your own?

Sales. So I was running sales and then jumped into the director of sales, strategic partnership roles, etc.

But my whole M.O. with the fractional world was truly business strategy and understanding what’s going to work best. And that could have been within the CTO space, CIO space, into the CFO world. As I jumped in between different fractional teams to really understand the lay of the land.

Yeah. What’s interesting is a lot of business owners, when they have that kind of diverse background like yourself, I find that they’re a little bit more successful because they understand all the elements of everything. Especially if it’s sales versus individuals that come from just IT or engineering or something like that. It makes it harder to jump into that world. Was it then not very difficult for you to jump into the entrepreneurial market as a business owner of your own?

It definitely happened on the fluke side of things. However, way back when, I worked for my father, who owned a gun shop years back. He opened it in either ’59 or ’69—one of those dates.

And what spurred this whole motion of thought was that you don’t have to do the typical behavior. You can look outside of the box. You can always discover a new way of saying hello in a different language, right?

My mind was always shifting and rolling with just conversations with my old pops, right?

Where things really took a dynamic turn was when I was at the fractional CTO firm. We ended up really crafting a new way of providing service, which then had me stepping back and thinking, maybe there's something here that I could innovate or change the game.

We wanted to show that communication between IT departments and C-suite individuals could actually work and that IT was not just a cost center.

That’s where the journey really began. I started a little startup and worked on that for a good chunk of time, which then stirred into various connections with investors, other founders, and the community. I just jumped into that world, not really knowing that it was a world to begin with. But that was really the catalyst that spurred it all on.

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The Concept of Sht Pitch*

It's interesting because I want to get real heavily into this new out-of-the-box idea you have with your pitch event. I think you laid the groundwork for it. In other words, you've been an out-of-the-box thinker for a while. Was it an aha moment when you started Sht Pitch? And I’m sure people are doing a double take, thinking, “Is he saying that right?”*

So let’s start with this—what is Sht Pitch? And then let’s back up and help me understand—did you have an aha moment with this, or did it slowly transition into it? How did you lead yourself into this world of what you’re currently doing? And then we’ll break it down.*

Okay, I'll give you the summary—the two-second version of Sht Pitch*. Sht Pitch* is about showing the human behind the startup—showing off more of the jockey than just the horse.

A lot of investors in the community and abroad don’t just look at the business pitch deck, its valuation, or its requirements. They’re looking at who is running it behind the scenes. And that’s really critical because those are the individuals that either make it or break it.

To answer your second question—how did this start? I was working with a really cool group of angel investors and VCs here in Utah, and we were all thinking the same thing: We’ve got to change the pitch and the narrative of what pitch events for entrepreneurs and investors are all about.

Are we actually doing everybody a service, or are we doing them a disservice with what we’re currently doing?

Because nine times out of ten, every investor could look at a pitch deck, compare it to the over-rehearsed business pitch given by the founder, and say, “Great, I could have just read that on my own.”

So I got a group together, and I said, “Let’s throw out this wild, crazy idea and experiment. Let’s just have some fun. Let’s be human for once and see what happens.”

They brought some founders, I brought some founders, we tossed them on stage, and at first, it was different than what it is today. But the whole premise was: let’s make sure they have time for their real business, like a normal pitch event for entrepreneurs. But let’s also give them something that they’re not prepared for—something that lets us see more of who they really are as people.

We give them a really bad idea, completely impromptu, and it’s a ridiculous idea that shouldn't exist. So nobody is investing in these, don’t worry.

But what we’re doing is putting these founders in a position to show off—how do they communicate? How do they work through a problem? How do they adapt? Can we see a little bit of that behavior?

Instead of just a lunch talking about their business, we see their energy, creativity, and how they handle challenges.

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The Human Element in Pitching

I love it. What’s so crazy is that I love that overview, and I had so many questions. I was going to jump in, but I wanted to get the full deal first because now we can go back and unpack it a little bit. I think it's brilliant, and I think you're right—it’s morphed over time. But it starts with this premise that I’ve had in all the companies I’ve built, in raising funds, and in working with investment funds. The idea that most true investors, in the end, will always look at the numbers. But they invest in the people more than the product.

You could have an amazing product and a horrible founder—or vice versa. So, I think it's a great point for listeners to understand that the person behind the business is just as important. That’s why with our authority marketing company, we emphasize that founders need to be visible. They need to be out there. So I love that.

You were already working in this space. What made you transition from focusing just on the business pitch to saying, "Let’s throw that out the window and do something different"? Was it a fluke idea? Was it something you felt was missing? What was the moment that made you decide to take this angle?

I think it came down to exactly what you just mentioned. Every big name behind you on your board has gone through a systematic approach to personal branding or personal awareness, right? But a lot of early founders don’t get that shot.

So we thought, How do we help these founders really show off who they are as human beings?

Through creative conversations and brainstorming with different investors, this idea surfaced as an experiment. I told everyone, “Let’s just try this out.” Even to the founders, I said, “Let’s play a little game. Worst-case scenario, all you’ve had is more time in front of investors.”

And it worked.

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Breaking the Facade: Humor, Adaptability, and Pressure

It’s genius because not only do you get to see their skills—how they adapt, how they think on their feet—but you also get to see their personality. Their humor, their ability to communicate under pressure, all of it.

And especially today, with AI and everything looking so polished and perfect, I think people crave authenticity. This breaks the ice and forces them to be real. What made you decide to also bring in that improv-style humor? Because it almost feels like an impromptu comedy show, but with real business implications.

That’s the funny part—I’ve had extroverts get on stage and be very serious, and I’ve had introverts who were absolutely hilarious.

I’m not funny, so I leave the comedy to everyone else. But for those that want a pressure cooker, Sht Pitch* definitely delivers.

And here’s the thing—people are naturally more relaxed when they’re in a room watching something lighthearted versus something overly serious.

So I thought, How do we bridge that gap?

The bottom line is, you're doing that. And I thought this was brilliant—you have them do this before their real pitch. So investors get a feel for them before they go into their actual business presentation. Do you feel like they try to maintain character knowing their real pitch is coming up, or do you really see them open up? What do you do to put them at ease so they don’t hold back?

It’s tricky because everyone is so different.

I tell them before they go on stage, “I’m not going to dictate how you should do this. What we want to see is you. I’m going to give you a topic, and it’s up to you to decide how it should be presented.”

That gives them the freedom to either show off their skills or, in some cases, try to mimic someone else—which usually backfires.

Nine times out of ten, if they try to imitate someone else’s style, they flop. And we all see it.

But Sht Pitch* is not a comedy roast. That’s important. We’re not roasting founders. We’re showcasing opportunities. We’re revealing how people communicate under pressure, how they handle unexpected situations.

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Investors Reading Between the Lines

We've had investors approach founders afterward and say, “Hey, you seem more like a COO than a CEO. Have you thought about different roles within your company?”

It’s about understanding people, not just the business structure.

That’s the real insight—what makes an effective economy is understanding human behavior. And when we do that right, we actually help founders position themselves better for long-term success.

I love that. And I wanted to dive deeper into one thing you mentioned earlier—where you said investors can see if someone is lying or stretching the truth during this process. What did you mean by that? And why did you choose to bring that specific aspect into the pitch format?

I'll give you an example.

We had a founder on stage at one of our CNBC-filmed events. His impromptu topic was Silent Karaoke. It was supposed to be a joke, right?

But instead of going the comedic route, he said, “I’d like to take a different angle. I have a family member who is deaf, and I want to pitch this idea as a real solution.”

And he did.

His delivery had me tearing up. I looked around the audience—there were actual tears.

Now, obviously, there were half-truths in his pitch because it was a fake idea. But it showed how he communicates, how he builds emotion, how he works through a challenge.

And that’s what investors need to see—how do you sell an idea when you don’t have all the answers?

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Insights on Successful Founders

It’s crazy because, at the end of the day, what you’re really uncovering is their ability to adapt. That’s a crucial skill in business. You’re not just testing their pitch—you’re testing their thinking.

With all the founders you’ve worked with, have you noticed any common characteristics among the ones who are really successful at raising money? Are they usually the natural-born entrepreneurs, or do you find that success comes from something else?

I'd say there are diamonds in the rough.

Some first-time founders come in and absolutely dominate an investor conversation. They can pull investors through their story and get them engaged. But for most founders, success comes down to experience, iteration, and validation.

And my philosophy is this: Most early-stage founders should not be looking for direct investment.

Not because they don’t have a great idea, but because they often haven’t validated it enough.

A lot of founders get caught up in the mindset of I need funding now, but the reality is—do you have LOIs (Letters of Intent)? Do you have a customer base? Have you validated the business model?

Too many entrepreneurs spend all their energy chasing investment before they’ve built a foundation, and that’s where they get stuck.

That’s such a great insight because I think most founders assume that the moment they have a great idea, they should immediately seek funding. But what you’re saying is, hold off—get some proof of traction first.

Exactly. The founders we put on stage are usually at the seed and Series A levels, because by that point, they’ve already started generating revenue.

If a company isn’t generating revenue yet, the only exception we make is for life sciences or med-tech companies—because those take longer to reach profitability.

But for other startups, revenue matters.

That’s why, even though we let pre-seed founders participate in the event, they need to have momentum. They need to show progress.

So what’s the number one trait that you’ve seen among founders who actually get investment?

Action.

It’s always about action-driven execution.

I’ve seen founders who weren’t the best public speakers, who weren’t the most charismatic, but they got funding because they could prove they were making things happen.

They weren’t just talking about their vision—they had actual data, traction, and milestones to back it up.

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The Difference Between Selling a Product vs. Pitching an Investor

That’s huge. Because I think most founders assume that if they can sell their product, they can sell their business to an investor—but that’s not always the case. What’s the biggest difference between selling your product and pitching to an investor?

It comes down to three things:

1. Storytelling – If there’s no compelling reason behind what you’re building, investors won’t connect with it.
2. Team – You need to know who is on your team, what gaps exist, and how you’re planning to fill them.
3. Capital Strategy – Investors want to know exactly how you plan to use their money. You don’t need to have every detail figured out, but you do need to demonstrate intent and purpose behind every dollar you’re raising.

That last point is so important because a lot of founders just say, "We need $1M for growth," but they don’t have a clear plan for how they’ll allocate it.

Exactly. Investors aren’t just looking at how much you need—they want to know why you need it, how you’ll use it, and when they’ll see a return.

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The Most Memorable Pitches

You’ve done a ton of these events. What are some of the craziest or most memorable pitches you’ve had on stage?

Oh man, we’ve had some wild ones.

One of the funniest was Pigeon Messaging.

Pigeon Messaging?

Yeah! The founder was given the prompt pigeon messaging—just two words. He could interpret it however he wanted.

And he decided to go all-in on a secure data transfer service… using pigeons.

He started breaking down actual success rates of pigeon deliveries, their reproduction cycles, how long it takes to train them, and even how to encrypt messages onto pigeons.

The audience was dying laughing. But at the same time, he delivered his pitch so convincingly that people were actually engaged.

That’s insane! What was his actual business pitch after that?

He was actually working in banking and financial encryption technology—so the pigeon messaging concept was hilarious but oddly relevant.

That’s amazing. What about the inflatable arms pitch?

Oh, that one was great.

The idea was inflatable muscle arms for people who feel insecure at the pool. So instead of just regular floaties, they would look like buff, muscular arms.

The founder completely ran with it. He talked about the psychological benefits, the social confidence boost, even how they could be customizable for different muscle shapes.

That’s so ridiculous, but I love it.

That’s the beauty of Sht Pitch*—you never know what’s going to happen, but it pushes founders to think on their feet and show who they really are.

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What’s Next for Sht Pitch?*

This is so good. So tell me, what’s on the horizon for Sht Pitch? What’s coming up next?*

We’re doubling down in 2025.

Last year, we launched with 11 events across the country. This year, we’re doing 20 national events.

We’re kicking off in New York, and we’ll be hitting major cities throughout the year. Then, we’ll close the season with a grand finale event in Utah—a two or three-day event featuring all the winners from every city.

And we’re taking it a step further—we’re filming it as a TV pilot to pitch to major networks.

That’s huge! So this could turn into a full-fledged show?

That’s the goal. We’ve seen the impact these events have had, and we know there’s an audience for it.

The challenge now is bringing it to an even bigger platform and continuing to connect founders with investors in the most authentic way possible.

That’s incredible. For anyone listening, where can they go to find upcoming events and get involved?

Everything is on Sh*tPitch.com.

You’ll find the event schedule, details on how to participate, and opportunities for investors, founders, and attendees to get involved.

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Final Advice for Founders

This has been amazing. Before we wrap up, what’s your final piece of advice for founders—especially those looking to raise money?

Fail fast.

If you’re sitting on an idea, don’t waste years trying to perfect it. Talk to people, test the market, and find out as quickly as possible if it’s viable.

And don’t just talk to friends and family—they’ll either tell you it’s amazing (because they love you) or they’ll say it’s too ambitious (because they don’t understand your vision).

Instead, talk to people who are actually in the space—investors, operators, and people who’ve done it before.

That’s a killer takeaway. Kent, thank you for sharing all of this. I’ll drop links in the show notes so people can connect with you. This was incredible!

Appreciate it, man. Let’s do it again soon!

Absolutely. Thanks for tuning in, everyone. Have a great day!

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About George Wright III:

George Wright is a Proven, Successful Entrepreneur- and he knows how to inspire entrepreneurs, companies, and individuals to achieve Massive Results. With more than 20 years of Executive Management experience and 25 years of Direct Marketing and Sales experience, George is responsible for starting and building several successful multimillion-dollar companies. He started at a very young age to network and build his experience and knowledge of what it takes to become a driven and well-known entrepreneur. George built a multi-million-dollar seminar business, promoting some of the biggest stars and brands in the world. He has accelerated the success and cash flow in each of his ventures through his network of resources and results driven strategies. George is now dedicated to teaching and sharing his Prosperity Principles and Strategies to every Driven and Passionate Entrepreneur he meets. His mission is to Empower Entrepreneurs Globally to create Massive Change and LIVE their Ultimate Destiny.

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About Kent Richeson:

Kent Richeson is an innovative entrepreneur, investor, and founder of ShitPitch, a unique pitch event that emphasizes the human element behind business ideas. Through ShitPitch, he offers a platform where founders present both their actual business concepts and spontaneously crafted, humorous pitches, allowing investors to assess their adaptability and communication skills. Richeson has hosted pitch events nationwide, including one featured on CNBC, and is expanding ShitPitch globally, with events planned in countries like India, Australia, the UK, Canada, and Mexico. His approach is reshaping how founders and investors connect, focusing on authenticity and creativity in the entrepreneurial journey.

Guest Resources:

Website: https://shitpitch.com/

LinkedIn [Kent Richeson]: https://www.linkedin.com/in/kentricheson/

LinkedIn [ShitPitch]: https://www.linkedin.com/company/shit-pitch/

Instagram [Kent Richeson]: @KentRicheson

Instagram [ShitPitch]: @ShitPitch