3 Key Lessons From Real Entrepreneurs: Scaling, Branding & Reinventing | GaryVee Business Q&A

Summary

The GaryVee Audio Experience: Episode Summary

Episode: 3 Key Lessons From Real Entrepreneurs: Scaling, Branding & Reinventing | GaryVee Business Q&A
Release Date: March 12, 2025
Host: Gary Vaynerchuk
Duration: Approximately 32 minutes

In this insightful episode of The GaryVee Audio Experience, Gary Vaynerchuk delves into three pivotal lessons gleaned from real entrepreneurs grappling with scaling their businesses, managing brand identity, and reinventing their ventures. Drawing from the dynamic interactions at the 4DS immersive workshop, Gary offers actionable advice backed by authentic conversations with entrepreneurs striving to elevate their enterprises.

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1. Building for Scale

Entrepreneur 1 opens the discussion by outlining the challenges of scaling a SaaS (Software as a Service) business. Having achieved $160,000 in monthly recurring revenue within eight months of launching a subscription-based direct mail platform, the entrepreneur seeks Gary's guidance on sustaining momentum without compromising quality.

Key Insights:

• Flexibility in Goals: Gary emphasizes the importance of maintaining a flexible mindset regarding financial targets. He advises against being overly fixated on specific numbers, suggesting entrepreneurs remain open to adjusting their aspirations as the business evolves.

  "The first thing about that sentence is when I've noticed when entrepreneurs make those kind of ideologies, they dig into it and they tend to make mistakes when they have something good because of some arbitrary number." — Gary Vaynerchuk [02:00]

• Diversifying Verticals: Addressing the entrepreneur's foray into various service industries, Gary underscores the necessity of balancing profitability with expansion. While pursuing multiple verticals can expedite growth, it may also dilute focus and reduce overall profitability.

• Strategic Funding: When contemplating funding options, Gary advises prioritizing strategic investments that align with the company's vision and can provide additional business value beyond mere capital infusion.

  "If the funding can be strategic, it can be very interesting." — Gary Vaynerchuk [07:44]

Notable Quotes:

• "Make as little money as possible if you think you have a good business. The biggest mistake people make is they want to take money from the business instead of putting money into the business." — Gary Vaynerchuk [07:10]

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2. Balancing Identity and Growth

Entrepreneur 2 addresses the complexity of managing multiple brands and maintaining clarity without alienating the audience. With ventures ranging from drone tours to personal photography, the entrepreneur seeks strategies to seamlessly integrate diverse content streams.

Key Insights:

• Authentic Content Integration: Gary advocates for honesty and transparency in content creation. He encourages entrepreneurs to occasionally intertwine different aspects of their business, even if it means deviating from their usual content style.

  "The process of trying is the fun." — Gary Vaynerchuk [02:59]

• Prioritizing Business Over Aesthetics: Emphasizing the importance of business objectives over social media algorithms, Gary advises entrepreneurs to focus on what drives business growth rather than solely optimizing for aesthetic appeal or follower counts.

  "We have a logical business conversation right now. I'm like, what would you like to happen?" — Gary Vaynerchuk [15:22]

• Content Strategy Flexibility: He highlights the value of adaptable content strategies that prioritize engagement and business outcomes over rigid adherence to platform norms or visual consistency.

  "It's the business over algo." — Gary Vaynerchuk [16:37]

Notable Quotes:

• "Stick with me on that. You got me?" — Gary Vaynerchuk [11:56]

• "You need the first part to work." — Gary Vaynerchuk [14:38]

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3. The Power of Reinvention, Pivoting, and Fundraising

Entrepreneur 3 shares a personal journey of transitioning from a footwear designer to launching a mobile tailoring service, highlighting the challenges of pivoting industries and raising capital. Seeking advice on effectively communicating with diverse stakeholders and securing pre-seed funding, the entrepreneur looks to Gary for direction.

Key Insights:

• Leveraging Personal Networks: Gary underscores the untapped potential within personal contacts for fundraising. He recommends personalized outreach through varied communication channels tailored to different relationship tiers.

  "If you're raising capital, I think it's in your phone. Like literally." — Gary Vaynerchuk [26:10]

• Empathetic Communication: Emphasizing empathy in sales and pitching, Gary encourages entrepreneurs to understand and resonate with their audience's perspectives, fostering genuine connections that can facilitate investment and support.

  "Look, everything that is. Anytime I've ever wanted to sell anything, when empathy launched, when I had books v friends, I go into the rare occasion of empathetic sales mode." — Gary Vaynerchuk [28:21]

• Streamlined Fundraising Strategy: Advising against broad, unfocused fundraising efforts, Gary recommends a targeted approach that leverages strong, existing relationships and presents clear, concise value propositions to potential investors.

Notable Quotes:

• "You're not gonna convince people to be more ambitious. ... Don't convince, just have conviction." — Gary Vaynerchuk [17:27]

• "Make different videos. ... What's the alternative?" — Gary Vaynerchuk [28:02]

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Conclusion

Throughout this episode, Gary Vaynerchuk imparts essential lessons on scaling businesses, maintaining brand integrity amidst growth, and successfully pivoting ventures. His pragmatic approach advocates for flexibility, authentic engagement, and strategic utilization of personal networks to navigate the complexities of entrepreneurship. By addressing real-world challenges faced by entrepreneurs, Gary provides a roadmap for sustained business growth and innovation.

Final Thoughts:

Gary consistently emphasizes the importance of focusing on tangible business outcomes over superficial metrics. Whether it's scaling a SaaS company, balancing multiple brand identities, or reinventing a business model, the core message revolves around strategic investment, authentic communication, and unwavering conviction in one's vision.

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This summary encapsulates the pivotal discussions and advice shared in the episode, offering a comprehensive overview for listeners seeking to glean actionable insights from Gary Vaynerchuk's expertise.

Transcript

[Gary Vaynerchuk]

Yo, everybody. Thank you so much for listening to this episode. It would mean the world to me if you could leave a review for this episode and back to the show.

[Unknown Host]

Hey, everyone. Today's episode of the Gary Vee Audio experience is curated from the most impactful moments of 4Ds. The 4DS is a two day immersive workshop at VaynerX HQ in New York where business owners get real time advice from Gary. The three clips that we have for you today each tackle a different challenge. If you're struggling with scaling your business, your content strategy, or you're even trying to reinvent yourself as a brand, this is the episode for you. First up, we have building for scale. How do you grow without losing momentum? Let's hear from the first entrepreneur as they break down their challenges. For Gary, my question is leading towards scale.

[Entrepreneur 1]

So we've been in business three years. We started selling subscriptions about eight months ago. We got to 160,000amonth in recurring revenue in eight months.

[Gary Vaynerchuk]

What subscription?

[Entrepreneur 1]

So we sell a subscription to our direct mail platform, the software that we build.

[Gary Vaynerchuk]

Got it.

[Entrepreneur 1]

So who would have told us?

[Gary Vaynerchuk]

So it's a SaaS product.

[Entrepreneur 1]

100%?

[Gary Vaynerchuk]

Yeah. So I just subscription, leave it on.

[Entrepreneur 1]

A print shop and say, you're fucking crazy. That's not a plan at all. We tried fulfillment partners, we tried all the other shit. They're a piece of equipment. They have manuals. We hired humans to put it all together. So we do it all in house.

[Gary Vaynerchuk]

Yep.

[Entrepreneur 1]

Huge in home service right now. So my background, I have a cleaning company we've had for 12 years. We leverage that a lot. I've been doing the public speaking, the trade shows. We come out with products in that space and it's working. We fucking hate it.

[Gary Vaynerchuk]

It's painful.

[Entrepreneur 1]

So like the mom and pop, the customer service, it's the same fucking conversation from Chuck in the truck, who started yesterday, all the way up to a $500 million roofing business. Like, there's no predictability.

[Gary Vaynerchuk]

Yep.

[Entrepreneur 1]

So looking towards scale, we want to sell this company for 500 million by the time we turn 40. That's in three years.

[Gary Vaynerchuk]

I would tell you right off the bat, the first thing about that sentence is when I've noticed when entrepreneurs make those kind of ideologies, they dig into it and they tend to make mistakes when they have something good because of some arbitrary number. Like why not 750 million by the time you're 38?

[Entrepreneur 1]

Cause we keep putting a number to it and it's gotta Keep going up.

[Gary Vaynerchuk]

I get that. Just make sure you have a good relationship with it. I think with that number. Yeah.

[Entrepreneur 1]

Can it change?

[Gary Vaynerchuk]

Of course. That sounds like a good relationship with it. I just have noticed a lot of people make these crazy numbers. Like, when I'm 35, I'm gonna sell this for 100 million. And then when I've watched it, I'm like, fuck. They were well on their way to building, but because they fucking put this outcome on a pedestal, they did this M and A deal and then they did this and it all kind of unraveled. So, you know, just even you saying, can it change already? Made me feel a hell of a lot better. Like, having ambition is an incredibly beautiful kind of framework. Sometimes people dig a little bit too deep into numbers and it changes their decision making and it hurts them. So keep going.

[Entrepreneur 1]

The number's so trivial for us. Like, I want to say a billion.

[Gary Vaynerchuk]

I said, it's kind of like the jets thing for me. Like, I will be very okay if I don't buy the Jets. Like, beyond. I'm okay now forever, for the rest of my life. The process of trying is the fun.

[Entrepreneur 1]

Dude, we sell it for 100 or whatever the fuck. Got it. Keep going.

[Gary Vaynerchuk]

Keep going. Yeah.

[Entrepreneur 1]

The idea is that, like, we see the home service space, we see the scalability. James, you had said something at dinner last night about, like, not killing the golden goose. So we can't just pull out a home service. Getting into cannabis real big. They can't send, they can't fucking advertise online. They can't do anything. We're doing huge stuff with mail with them and practices and shit.

[Gary Vaynerchuk]

Yep.

[Entrepreneur 1]

QR code, straight makes sense. Aggregating lists, all that type of shit.

[Gary Vaynerchuk]

Smart.

[Entrepreneur 1]

Also full time. And agencies. Really well. So we're not threatened.

[Gary Vaynerchuk]

Of course. You're the back end.

[Entrepreneur 1]

Exactly.

[Entrepreneur 2]

We were.

[Entrepreneur 1]

We were debating with, like, do we do a white label or not? And Connor, the rational one in the relationship is like, dude, it's the ads. We're like, the agency Vanderb isn't gonna want to have their clients get an invoice from dope.

[Gary Vaynerchuk]

Right.

[Entrepreneur 1]

Who do you get the fucking invoice from when you're on Facebook? Ads?

[Gary Vaynerchuk]

Yeah, of course, of course.

[Entrepreneur 1]

The ad spend or whatever.

[Gary Vaynerchuk]

Yep.

[Entrepreneur 1]

So as we look towards this acquisition, whatever that number is, you know, it's easy to set a metric of 40 being a goal or whatever.

[Gary Vaynerchuk]

Okay.

[Entrepreneur 1]

As we build towards that path, what would your advice be about? A focus as like, so we tie in with CRMs, send Dave the roofer to a job, get a job approved. 50 postcards. Go to the neighbor. We shot your neighbor Approved. Mark the job scheduled. Another 50 plus cards going, pardon the dust, pardon the noise. We're working in. And it works for every fucking vertical. So what we say internally, if it's timeless, we. We spend time on it. Rounds as covered wagons.

[Gary Vaynerchuk]

We want something to do with it.

[Entrepreneur 1]

So the idea is like. Or my question first one is, where would you focus time? Is it all of them? Is it one of them directly?

[Entrepreneur 2]

Would you.

[Gary Vaynerchuk]

You mean the service industries?

[Entrepreneur 1]

Yeah, service industries.

[Gary Vaynerchuk]

We look at relative.

[Entrepreneur 1]

There's about 70. You want labor, you run equipment. Or somewhere between relative conversation. Cannabis agency.

[Gary Vaynerchuk]

I see home services. My intuition. In this scenario, off of what I'm reading, the answer would be all of them. But it would require you to be less profitable each year. Well, what James knows is Vayner made no money for three years in a row. Most people don't have that appetite, which is why they can't build big companies.

[Entrepreneur 1]

So what if we don't give a shit about that?

[Gary Vaynerchuk]

Then go to every vertical, just hire more people and make no money. Yeah. It becomes a game of, hey, are we. You know, I don't know what you're doing with the profits. The company's an llc.

[Entrepreneur 1]

We're growing.

[Gary Vaynerchuk]

Yeah, right. So, like, you're gonna get taxed on that and you're gonna, like you're distributing to yourselves at the end of the year. Distribute less so you can be in more verticals fast. Great. So then it's. So then it's just maximize your profits to reinvest in people so that you could have heads of verticals and go hard at every vertical that you see opportunity in.

[Entrepreneur 1]

What do you see in the cannabis space as far as the opportunity?

[Gary Vaynerchuk]

I think it's gonna be one of the top 10 consumer products in our society.

[Entrepreneur 1]

How do you feel about mailing the candidate space?

[Gary Vaynerchuk]

I think while Facebook and Google are giving you an opportunity for land grab, you should go as hard as fucking possible. Because in about 40 minutes it's not going to. And you'll lose 80% of your market. You know what I mean? I think for that one specifically. Cause it's so unique. Out of everything we're talking about, you should go incredibly hard.

[Entrepreneur 1]

How would you push agencies?

[Gary Vaynerchuk]

Agencies are easy.

[Entrepreneur 1]

We have a lot of agency relationships.

[Gary Vaynerchuk]

That's why you already have. They're the easiest. They don't want to do shit. They want you to do all the work and they want to take a skim off the top, they're the easiest. That's why I hate them.

[Entrepreneur 1]

Equinox.

[Gary Vaynerchuk]

Yeah, you know, like, yeah, you know this agencies are thrilled to be a toll booth. Do nothing, have, you know, make a margin on top of what you do and call it a day. They're. You should get all of that.

[Entrepreneur 1]

Would you opt for those big ones or the little ones?

[Gary Vaynerchuk]

Little ones are easier, I think Cause big ones can have politics and like are dopey.

[Entrepreneur 1]

Would you take their leverage? So like Chris, we love Chris equally.

[Gary Vaynerchuk]

Right.

[Entrepreneur 1]

But Chris is like, I could change your life. I'm like, chris, would you do that for me? You promise? Like they come with that ego shit with it.

[Gary Vaynerchuk]

Yeah. I would say an unemotional service provider.

[Entrepreneur 1]

Small to mid or go after the big ones again.

[Gary Vaynerchuk]

This becomes a game of opportunity. Like at your level. Like to me it's, you know, I'm going through this with be friends. Right now we have 29 people. We're probably gonna have 130 in September. I'm about to hire 100 people.

[Entrepreneur 1]

What's the best advice you can give to someone?

[Gary Vaynerchuk]

Make as little money as possible if you think you have a good business. The biggest mistake people make is they want to take money from the business instead of putting money into the business. Now everyone has different circumstances. You know, some people have $400,000 in debt. Harder for that person to stay chill than someone who like so. But the longer you can hold your breath if you have a good business and pour it back into the business, the bigger your business is going to be.

[Entrepreneur 1]

So we debate right now with funding, we're pretty liquid right now. Do you take and carve out 10% equity to use leverage with that or are you just borrowing money as opposed to taking funding?

[Gary Vaynerchuk]

I think if the funding can be strategic, it can be very interesting. Right? Yeah. Which is really sometimes hard to tell up front. There's a lot of trickiness to that. But if you're, when you say you're liquid to me, if you decide to take the concept that we're talking about and hire a lot more, all of a sudden having more cash at your disposal is pretty interesting. I think credit lines are interesting. We forget about that nerdy simple thing called credit lines. You know, I think, I think, but I do think funding at times can work. I think money is the commodity for a good operator. I think finding someone who's strategic, who can get you more business is interesting. Example if a family owned a private business of the biggest service provider, like that's where you want to go because immediately once they invest in you, they're also going to give you all the clients. And so it's like you get a double bite at the apple. So look for that kind of person.

[Entrepreneur 1]

Any verticals that we're missing that if you had your head on this that you would be looking for right now.

[Gary Vaynerchuk]

So this is direct mail.

[Entrepreneur 1]

Automated direct mail. No minimum order.

[Gary Vaynerchuk]

That's really cool. Influencers. I think if you educate influencers through TikTok ads that it's almost like the ad is really funny. It's like hey, I know this is gonna sound crazy. You know what I mean? Like I know this is gonna sound insane if you're an influencer. But running direct mail in your local area for like pop ups or events like it just might become ironic enough when I hear no minimum. Everyone should almost try it. I would. I also think that people don't like direct mail in a world where iOS14.5 has changed has more leverage than it used to. And so yeah, I mean E Comm already does it. I assume you're over in there. Yeah, I think the weird ones are influencer for sure. I think is a weird one. I think most influencers will struggle with it. But if you get momentum. What's cool about influencers is that world is small. If God forbid Emma Chamberlain does it and works for her coffee. Like all of a sudden everyone's doing it and it can get real big real fast. That's the one that probably stands out as like a weird one micros and.

[Entrepreneur 1]

Just get them fucking.

[Gary Vaynerchuk]

Yeah. And I think in your business if you're running on the kind of margin that you should be on a SaaS model you should be doing like trial low cost stuff like it's just worth it for acquisition.

[Unknown Host]

Up next we have balancing identity and growth. How do you manage multiple ventures and brand clarity without confusing your audience?

[Entrepreneur 2]

So kind of set up our content the way it runs. We have epic drone tours, brand platforms and then my own personal. Our own personal brands. Then I've got my photography on the.

[Gary Vaynerchuk]

Side which makes sense.

[Entrepreneur 2]

Pretty big following but strictly swimming. So I should just share photos there.

[Gary Vaynerchuk]

But what you, what you can't fear is the occasional right hook of like we interrupt these normally scheduled programming to tell you I fuck with drones too. And let me give you a preview. Cause I have to do this and it's humbling cause nobody even the most secure at the top of the game. And you know this right? Like you see me on the team chat. I will post shit that I have to do that I know won't do well, but I have to do it. I want to see my normal 500,000 to a million views too. But I will take my 80,000 because I have to tell you that Sasha wants you to sign up for WineText and it's not fun to get 80,000 views. But I'm in the business to help my dad get you all to sign up for wine. Which by the way, you should all do that if you buy wine.

[Unknown Host]

Sorry guys, don't mean to interrupt the podcast. But for real, if you're not already signed up for winetext, you definitely should be.

[Gary Vaynerchuk]

You're right now scared to fuck up the algorithm. You're picking the algo and your subconscious insecurity of hitting your numbers over getting two customers from your photography world into your drone business. Isn't that wild? And you are like one of everybody else. So the people that got four things going on fuck up the thing that you have the most followers on from your ideology for the practicality of your business.

[Entrepreneur 2]

That's true.

[Gary Vaynerchuk]

Stick with me on that. You got me? Yeah. Like if your photography thing is your biggest platform, they won't love it, but they love you. And if you're honest with them, be like, you gotta make the right piece of content. If you just post like a flyer and be like, sign up for the drone. They're like, if you're like, hey, real quick, I know I'm fucking up. Like you're self deprecating. I know like what you want me from here. Just FYI, I realize a lot of you don't fully know me. Let me tell you about myself. I do this and that and I grew up like, got it.

[Entrepreneur 2]

Do you keep those? Do I keep those separate from you can where I do all the talking head and all that, or.

[Gary Vaynerchuk]

Look, I first of all, and a lot of you have followed me for a long time. I was always the one that was challenging you, like do it all in one place. Da da da. Like I was always fucking people up. Now I'm set. Cause it's all based on the content. Doesn't even fucking matter. You want a wildcard, Start a new account. It doesn't matter. You wanna really get fuckin liberated. It doesn't matter. Yeah, it's a real brain fuck to go from what we've been to where we're at. It's the content. It's the fucking content. So I think if you're respectful of your audience, disrespecting your audience and your photography is putting up A fucking epic, like, flyer look stupid, like, you know, like a piece of shit post. We all know what that is, right? Like a picture that's like, fucked up and like, sign up now. Like, like bad. You making a video, you know, and maybe a double setting, like the camera and the drone in your hand and just talking and being open with your audience to your photography. That's gonna work. Keeping them separate or not. I'm literally agnostic. I think at some level it helps people organize. I'm, like, very chaotic. I think a lot of people, like, they over. You know this. A lot of you are getting fucked up because you care about aesthetic. You want your grid to look right. Nobody gives a fuck about your grid, you know, Meaning I get it. Like, I don't want to discredit people going to a grid and getting like, I love brand, but fuck, man. 90% of the action's in feedback. So if you're doing grid for the aesthetic, but it's not following, best practice to reach the most audience in feed to what you're trying to do, what the fuck are you accomplishing? You don't get it, Gary. I want people, when they come to my account to see it, right? I'm like, they're not coming to your account because you're trying to make them look. Make it look right. You need the first part to work.

[Entrepreneur 2]

Awesome. So then for Epic dronetra specifically, we do a really good job of sharing. Our videos are dope.

[Gary Vaynerchuk]

Of course, they're epic.

[Entrepreneur 2]

And then we do really well with pilots.

[Gary Vaynerchuk]

You like that? That was good. Give me some for that. All right.

[Entrepreneur 2]

And then we do really well behind the scenes. We show all of our pilots flying. We travel across the country. So we try to get as much content. Very cool as possible. They also send me iPhone, videos and stuff.

[Gary Vaynerchuk]

Love.

[Entrepreneur 2]

But what's the. I feel like we have.

[Gary Vaynerchuk]

What else?

[Entrepreneur 2]

Jab, jab. What's the last. Like, what's value?

[Gary Vaynerchuk]

What do you want to happen? Let's take a big step back. What would you. When you post something on social, what would you like to happen?

[Entrepreneur 2]

Get customers, obviously, but no, no, no.

[Gary Vaynerchuk]

This is like a good game. Play with me. How many of the posts would you like to do that?

[Entrepreneur 2]

One every ten would be good.

[Gary Vaynerchuk]

So this is a good game because one could answer all of them. One could answer one of them. There's a lot of ways to think about this. There's no right answer. So let's say if you're thinking that way, which in a lot of ways, I think of it both ways I think in those terms too. Jab, jab, jab. Right hook, right. But even when I like, I know that the other nine are building awareness and they may click the URL in my profile. In theory, all good content could be doing the sale. But back to you saying the sale. Back to me saying I'm gonna fuck up my grid. Sign up for WineText right now. Do you guys go hardcore for the ask for business on every 10th post that? Do you see what I mean? I'm telling you, there is a disease in marketing. It's called caring about the vanity metrics over your business. We're having a logical business conversation right now. I'm like, what would you like to happen? You answered, really thought like I liked your answer. I think it's one of the smart places you could have gone. But you're not doing it because you're caring about the vanity. Meaning you don't even like you're caring about the algo. It's algo over everything for everyone. And for me it's business over algo.

[Entrepreneur 2]

But then what's the business? Well, I guess it's hard.

[Gary Vaynerchuk]

Well, how would you talk. How would you talk to me if you wanted me to buy your shit?

[Entrepreneur 2]

That's I guess kind of what we're, what we're figuring out is like we can give the, you know, you increase reach by having better videos. It builds a better brand for the companies because they're doing something nobody else is doing. Is that enough?

[Gary Vaynerchuk]

Of course it's enough. What you're uncomfortable with is getting enough nos to make you question if it's enough. VaynerMedia gets 90% nos, 10% yeses.

[Entrepreneur 2]

So then what? How? Because I think the people that we've worked with so far are the capturing the demand. It's people that are the go getters. They're doing the new thing.

[Gary Vaynerchuk]

I have good news for you. You're not going to convince people to be more ambitious.

[Entrepreneur 2]

So is there a way to kind of create the demand by I guess, I guess we have a better hard time getting the people that aren't already looking for what we do.

[Gary Vaynerchuk]

You haven't even gotten remotely enough of a percentage of the people that are looking. You're worried about convincing the non commensable and you haven't even gotten 1% of 1% of 1% of the commenced. You got it, my brother. One of the great things, I really appreciate you understanding what just happened. I would argue that I'm not sure if there's another thing bigger to my Professional success than. Than having the subconscious understanding at a very young age that you can't convince the unconvincable. Don't convince, just have conviction. I've been selling social media since 2009. How old were you in 2009?

[Entrepreneur 2]

12.

[Gary Vaynerchuk]

Good. When you were 12, I was walking around this earth trying to sell social media services. Nobody wanted it, but I believed and I found a small group that wanted it. And. And that's why we did $1 million in revenue the first year.

[Entrepreneur 2]

Awesome. So you talk a lot about the consumer segmentations. We, as I kind of mentioned, we have the same services that we do, but name 20 different.

[Gary Vaynerchuk]

Correct. The sentence you're going to say to a hotelier is going to be different than. Right. That's why I say the same thing 73,000 times in 100 different ways.

[Entrepreneur 2]

So how do you. A feedback we have gotten is a lot of people that we're talking to come to our page and they're like, oh, they only do commercial real estate. If they don't immediately see themselves, then they kind of assume that we can't help them. So how do you.

[Gary Vaynerchuk]

Well, then list them all. Like, I don't know what the website looks like, but literally it could be.

[Entrepreneur 2]

Like we have that website and we're talking social. It's like when they. Well, then if we do a cool shoot with the Padres for. We got four posts on the Padres.

[Gary Vaynerchuk]

Well, why don't you have the bio say like drone footage for anyone and any business.

[Entrepreneur 2]

That's good.

[Gary Vaynerchuk]

That's a good idea. Well, I didn't get here because of my looks.

[Entrepreneur 2]

And then last kind of one. So for a while I've always. I've been the one posting on social and being front, which I want to do for myself. But we're pretty soon going to be. We are in the process of hiring social media manager, strategist, whatever. What is the best thing to have them start right at the beginning. Like I can have them do 20 things, but what.

[Gary Vaynerchuk]

Well, I think if you're going to hire someone, I think you want to ask her or him what they think.

[Entrepreneur 2]

Find someone that doesn't say to have a better grid because that's what I'll do.

[Gary Vaynerchuk]

Right. If somebody said like, like this goes back to having a good strategy yourself. That's what you're here doing. Correct. Like some of you now will actually like all of a sudden that becomes your radar. I meet people all the time, I talk to people all the time. Like I get pitched to join vaynermedia at the airport while I'm ordering a coffee and I'm weird, I'll talk to them. And when they're like, I can make your grade. Great, they're out.

[Unknown Host]

Finally, we have the power of reinvention, pivoting fundraising, and breaking into new industries. Let's get a little bit more context from our next entrepreneur and see what Gary has to say.

[Entrepreneur 3]

So, so far, lots of great things to cipher through. So my background is I was a footwear designer for 17 years. I've worked for Beyonce. I've worked for Kenneth Cole. I've done all this great product. And actually, Joe's wife is in the footwear biz as well. And so coming up with this company, my joke is always that I have a landfill out there with my name on it. I was building all this great product. I was building product for Costco and Payless and Marshalls and TJ Maxx, and I found myself in this position of, like, what now? Like, I've been doing this for so long, and I'm not feeling passionate about it anymore. And happy circumstance ended up in a master's for sustainability and had a task Rabbit come to my apartment. They helped me go through my closet, and they pulled out this bag, and they're like, what is this? And I was like, oh, that's alterations I have to do. And they're like, are you gonna do them? I was like, so I ended up donating them. And I looked back at that. I'm like, wait, hold on. I'm literally in a Master's for sustainability. I love fashion, and that bag probably had the best things in my closet that I had a story for to tell, and I wasn't telling it. And so I started asking people, well, do you have a bag in the back of your closet? And it was either the trunk of a car, the back of a closet, and Kate's one of our customers, and for her. And I was part of that luminary community. And so we started seeing this opportunity that every single person here has something in their closet that something is wrong with, whether it's a tear or a button and anything. So how do we solve that problem? So for the customers, I've asked you that question.

[Gary Vaynerchuk]

So smart.

[Entrepreneur 3]

Thank you. For small businesses, you have mom and pop shops who are being totally, you know, broken by this technology that's helped air and travel and all these things, but they're left behind. So my question is going to be small brands, customers brands, easy. We're taking their budget dollars for sustainable initiatives and effectively using them to badge them with local tailors. So Macy's, you buy something in New York, but let's say you bought it online and you live in Kentucky. How are they connecting you with a tailor or a cobbler in your location that you can connect with? And so finally the planet we, you know, if you can extend the life of your clothes by just a few months, you can actually increase your decrease your carbon footprint by 20 to 30%. All that to say I have these four main stakeholders and I love them all so much. And we're about to start our pre seed fundraise. And my co founder, her background's engineering consulting. She's worked for luxury brands and data and analytics. And I'm the. I talk for a long time and I love what I do and I'm so happy and excited. How do I most effectively speak to these four stakeholders, speak to investors and create that roadmap for them? Because, like, my real vision is reinvigorating the industry through certifications and trainings and making it so sexy to repair and revive your wardrobe that we're actually taking these designers out of school who are absolutely like, I literally had no idea this is what designing was. And giving them the opportunity to work directly with people, people and learn from these, like skilled artisans who are not passing down their work.

[Gary Vaynerchuk]

Understood. With the purpose in the short term to raise capital.

[Entrepreneur 3]

Yes.

[Gary Vaynerchuk]

So I think that in the short term, there's only two ways that you would do that. One is go bananas on you being the face of the brand and doing content. Or two, you going through an exercise similar to the last one of. I do not think business people realize that almost all the gold is in their iPhone contacts from A to Z. It's really wild to me. Like when I think about, notice how like, you just gave a beautiful, like, statement that's the nicest thing anyone's ever seen. No, it's really, it's the reason I gave you the answer of maybe you should be making a lot of content. I think it would go well. But notice how when I got to speak after all of that, I just went right to the punchline, which is like, right now you need capital. And so I go to yes, I could tell you to start making unlimited TikToks and LinkedIn in seven months. You'd probably get inquiries. Or I could literally ask you to make a video or six. So they're not all the same and be like, hey, friend, I'm actually texting this to about 20, 30 of my friends on my cell phone to Tell you like, what I'm up to. If you, if you give me three minutes, just watch this. And you make like four different versions. Because obviously from A to Z you have the people you talk to often. Then you have tier two, then you have tier three. They haven't talked to in six months to a year, but you kind of know. And then tier four, you're like, I'm not even sure if I know this person. Right. You kind of need to make a video for all of them. And literally, what's your grandmonier? Water, wine, coffee? What do you drink?

[Entrepreneur 3]

Depends on the day.

[Gary Vaynerchuk]

Fair enough. Same. Literally, if you're raising capital, I think it's in your phone. Like literally.

[Entrepreneur 3]

Follow up question, please. I have been building this brand for the last.

[Gary Vaynerchuk]

I apologize for a second. And so for like all of you, literally, the video is like. And again, four groups, homies, kind of homies, know them pretty solid, but haven't talked in a year, have no fucking idea who this is. And making four different videos. And literally, literally for you, it's like, hey, I'm just doing business development. Hope you've been well, like, because remember, the first 13 seconds for those four groups are gonna be very different. Yeah. Hey, the fourth one. Hey, how you been? Just doing some karma out here. Wanna tell you what I've been up to. What I want, which is I want some customers on my shit. Hit me back with what you're up to. Maybe I can help you. Just some karma that's gonna land versus, you know, versus your first group were to text and be like, hey, I made this video for like my 25 closest friends. Watch it because you know you can get away with that with that video. Anyway, keep going.

[Entrepreneur 3]

So I've been building this for the last couple years and luckily I like thrive in the awkward. And I'm like, I have the goldfish memory. Like, I keep going. But what we built was a mobile tailoring company. And what we saw was that it's really labor intensive and asset heavy. And so I've always thought of it like, I have a quota to read with. With my friends and I through the pandemic, we built a New York City face mask initiative. We built, we made 40,000 masks for frontline providers using Taylor's because we were supposed to launch the company on March 20, 20. But it was really, it was an amazing, like, of course.

[Gary Vaynerchuk]

Happiness.

[Entrepreneur 3]

What is this community and family I've built? Here's the interesting thing that now I finally, I'm like, I get it. I know what I'm doing. And I feel like I've tapped.

[Gary Vaynerchuk]

Like you've tapped everyone.

[Entrepreneur 3]

Yeah. And I don't want to annoy people, but I also am like, no, I've got it now.

[Gary Vaynerchuk]

Come back, tell them the truth. Make different videos. You know that your best homie, you've actually like truly cried wolf, not only on this project, but through the years. And so that person's gotta hear something different than me who met you once at a conference and you have my info. Like, here's the bottom line. What's the alternative?

[Entrepreneur 3]

Yeah.

[Gary Vaynerchuk]

Like, as long as you're empathetic in your communication. Look, everything that is. Anytime I've ever wanted to sell anything, when empathy launched, when I had books v friends, I go into the rare occasion of empathetic sales mode and I go into a cocoon, sometimes a 20 hour flight. I've actually gone to our Asia office once because I had to work for 10 straight hours and didn't think I could do it any other way besides taking a flight to Asia. That's how hard it is to sometimes get into the zone for some of us. Other people. I really put. I've never done this. Actually, that's not true. When I had to do Vee Friends, I knew that I had to draw 250 people. I literally rented. Actually, that's not true. One of Mona's friends had a house in Malibu and was like, come and stay. And I went for a week with five or six of the crew and just drew. Just was creative. This is the biggest thing you're working on. You have to go off the grid and ask everybody from A to Z again in context, maybe for you it's 700 videos. Because every one of the people you've annoyed needs their own individual. I'm serious. And that's okay because here's my question. What's the alternative? This is the worst fundraising market we've had in forever.

[Entrepreneur 3]

Yeah.

[Gary Vaynerchuk]

The end. You're not gonna. It's so hard to raise capital. If you're gonna raise capital, the terms are gonna be obnoxiously bad.

[Entrepreneur 3]

Yeah.

[Gary Vaynerchuk]

So you have the option of getting a huge waste of time with bullshit VCs that won't give you the money anyway. Or you go back to the well. But notice maybe you've been on the kick of group one and two. You never know when group three and four, I mean, when I tell you in my group one, and I'm a giver, I've had people who I've like changed their app. I'll Just paint you a very clear picture. When I go to sell books, I've had people in group four that I've talked to once, forget about me being Gary Vee. I'll take it back seven or eight years ago where I was like, gary B. But, like, not this Gary B. Right? Like, nobody did it because I was cool. They kind of knew me a little something. I had people who I barely knew bought 50 books just because they're like me and they're on some karma shit and they're like, I got you. I had people in group one who. I got them. One person. As you can see, the passion's coming through. One person I went to bat for on an investment, reopened the funding round to get them in. It was closed. I put, like. I went out of my way. He put in 50k and made $13 million on that exit. And he bought zero books. And I was. And when I tell you I'm still very friendly with the person, that doesn't even register. I go into empathy. Like, maybe he was busy, maybe he didn't see it. I did him up four times because I thought it was good, because I thought it was gonna be a big one. Because, like, this man made a lot of money. He's gonna buy a thousand books. Like, I really took it. Like, you know, and. And. And, you know, some people don't see the world the same way. Like, I was mortified when I found out six years into traveling that you're supposed to leave a tip for people at the hotel. That was one of the worst days of my life in my entire life. One of the worst days was somewhere around mid-30s somehow. I don't even remember now. I was like, what? You know, because I didn't grow up traveling, I didn't know. I didn't. I never heard of it. I didn't know. It was, like the worst feeling ever in my stomach because I was very passionate about tipping. And I just. Sometimes you don't know the etiquette.

[Entrepreneur 3]

Yeah.

[Gary Vaynerchuk]

Like, you know, so, like, I was like, well, who am I to judge this person? I didn't know that every time I was in a hotel, I should leave something. I just didn't know. I knew if for a driver, I knew for someone taking out a package, I just didn't know. Maybe he doesn't know. If someone makes you $13 million, you should buy some books. You know, why am I telling you that's so long winded? You got to reset and you got to go with what's reality for you.

[Entrepreneur 3]

And my one follow up question again is in terms of accredited investors. So I've done my research, safe notes and this and what are you looking for? And that's the one thing is like if you want to end up in a VC and at some point we'll probably end up in like, like a circular VC for a circular economy. But we don't want to do it now. We want to do pre seed. We want angel investors, we want friends and family. But some of my friends are like how? And I've thought about crowdfunding and it's like all these questions of what's the best way to fundraise and you're saying go to these people. Do I want to go to them and say do you know anyone who's an accredited investor or do you want to.

[Gary Vaynerchuk]

Don't worry about the everyone who's an accredited investor knows credit investor comes from like how their financial status don't over. You're getting scared of something that doesn't matter.

[Entrepreneur 3]

But how do I. What if someone isn't one and wants to invest in us?

[Gary Vaynerchuk]

Your lawyer or whoever is helping you will figure that out. Most people, almost no one hits that realm because you're not asking for $500, right? You're asking for 10, 15, $20,000 minimum. And that's gonna knock most people into that realm.