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Tech beyond the valley.

Earlier this year, Mickey and Gary joined Matt Hunckler for the Powderkeg Unvalley Conference. Powderkeg is a network of local communities with global reach for tech entrepreneurs, investors, and top talent. Unvalley is a two-day virtual event that explores the untapped potential beyond Silicon Valley. 

Life is uncomfortably about perspective, and if you have good intent and you're capable, you're going to execute.

Gary VaynerchukChairman of VaynerX and CEO of VaynerMedia


Bonus: Mickey Cloud and Gary Vaynerchuk Talk Entrepreneurial Spirit and Attracting Talent to New Cities at Powderkeg Unvalley Conference


Julia Balick (00:04):

Welcome to this week’s special bonus episode of Building While Flying. We’re spotlighting an interview from Powderkeg’s Unvalley conference last month, featuring VaynerX CEO, Gary Vaynerchuk, and our very own Mickey Cloud, along with Matt Hunkler, founder and CEO of Powderkeg. Powderkeg is a network of local communities with global reach for tech entrepreneurs, investors, and top talent.


Julia Balick  (00:31):

Unvalley is a two-day virtual event that explores the untapped potential beyond Silicon Valley. We often ask ourselves, “Where’s the best city for me to live?” But our story asks a different question. How can cities attract new talent and companies? For Mickey, Gary, and the Sasha Group team, that means leaning into the entrepreneurial spirit and the big small town hyper-connectivity of Chattanooga. That is what makes up its DNA, and that’s just the beginning.


Julia Balick (01:04):

It all started with a visit in 2014 to the scenic city or gig city, thanks to its gigabyte internet. The rest, as you’ll hear from Mickey and Gary, is history. The origin story of the Sasha Group encourages us to ask how can you bring value to your community? After you listen, let us know on our Facebook, Twitter, Instagram, or LinkedIn. Now, buckle up for this special bonus episode.


Katie Hankinson (01:35):

Hi, I’m Katie Hankinson.


Mickey Cloud (01:37):

And I’m Mickey Cloud.


Katie Hankinson (01:38):

Welcome to Building While Flying, a Sasha Group podcast where we interview business leaders about how they tackle challenges, stay resilient, and navigate ever-changing skies.


Matt (01:55):

So please help me welcome to the virtual stage here at Powderkeg Unvalley, Gary Vaynerchuk and Mickey Cloud. Thanks guys for being here.


Mickey Cloud (02:02):

Thanks, Matt.


Matt (02:02):



Gary Vaynerchuck (02:02):

Thanks for having us.


Matt (02:05):

Absolutely. I’m super excited to have this conversation because I’ve heard little bits and pieces of the story, but I wanted to make sure we got the whole thing here for everybody that’s kicking off Unvalley bright and early for us. I’d love to hear how you guys met. Do you remember what that initial connection was like, and how you knew there was a spark there?


Gary Vaynerchuck (02:25):



Mickey Cloud (02:27):

Yeah, so it was fall of 2011. I was working in the advertising industry in New York and one of the first people I ever met in New York at an ad agency job, Elise Bartlett, had moved away from New York and came back and I was trying to help her find a job. Her aunt maybe read The Thank You Economy, and on the last page of The Thank You Economy, it says, “If you’re interested in doing this type of work, email info@VaynerMedia.


Mickey Cloud (02:56):

So Elise got hired pretty quickly in the summer of 2011 as the first employee that had come from an ad agency. Everyone else at the time was just basically AJ and Gary and folks that had gotten into their world. And then Elise reached out to me and said, “I want to catch up.” I was like, “Great, let’s get a beer.” She said, “Can you meet my founder at 8:00 AM on Thursday?” I was like, “I wasn’t expecting that.” But I got an hour with Gary, and that, I realize today in 2011 it was.


Matt (03:32):

I love it. Gary, do you remember your first impressions of that conversation with Mickey?


Gary Vaynerchuck (03:36):

Yeah, I do. With hiring Elise, we just had a… Mickey, do you know exactly what month it was?


Mickey Cloud (03:48):

We met in September of 2011. It was right after Labor Day, so it was right after you clicked in full-time.


Gary Vaynerchuck (03:53):

Right. So Matt, the reason, and everybody watching, the reason I asked Mickey that is that’s exactly right. Literally August 23rd of that year, I decided I was going to go full-time VaynerMedia, because at that point, it was really one foot in Wine Library, one foot in Vayner, my third foot in the emergence of Gary V with the books and the speaking. And then I had this incredible opportunity to start a vodka brand with a very, very, very famous person.


Gary Vaynerchuck (04:26):

And I was actually leaning towards that way the whole way. And then in late August, I had some time off and I said, “You know what? How is it possible that two years plus we’ve been doing this Vayner thing and yet none of these agencies are still doing what we’re doing, knowing how important it was?” And so it became very obvious to me that that was the right move.


Gary Vaynerchuck (04:49):

And so I decided to plug in and I then went on the offense of wanting to meet people from the actual ad industry, not just the disruptive DNA that we had. And Mickey was one of those first meetings and I’m quite intuitive. And to this day am comfortable in going with my intuition and saying, “Hey, let’s go deeper. Let’s go bigger.” And I mean, Mickey, I don’t know if it was the second meeting or that first meeting, but very quickly I was like, “Mickey, what do you want?” I went like, “What do you care about in life?”


Mickey Cloud (05:34):

It was 20 minutes into the first meeting that you asked that question. And my answer was I want to be back in the Southeast. I want to leverage my experience in New York in advertising and bring brands and startups. And once I said that, Gary was like, “Well, then why are you thinking about interviewing anywhere else? That’s my world.” And at the time, I had watched maybe one video of Gary before I met him. I didn’t know who he was.


Mickey Cloud (06:01):

And so we kept talking and by the end of that conversation, I remember this so vividly. He said, “Listen, if you can come give me four years here and do the things I think you can do, and I do the things I think I can do, in four years, we’ll get you back to the Southeast.” And I remember thinking A, “Who is this guy that would offer that?” And then B, “Why do I believe him?” Because in that moment, I just really believed him.


Gary Vaynerchuck (06:30):

And that’s so much of what I think I’m about and what feels real to me are narratives that I do understand that a modern, cynical, practical, I don’t even want to use it as a negative, society struggles with. But for me, when you’re a pure bred entrepreneur and I mean a pure bred, the reason Mickey believed me was because I was 100% in belief, and was articulating my truth. And I think as I’ve gotten older, especially in the last two to three years, it’s really become very clear to me that life is uncomfortably about perspective.


Gary Vaynerchuck (07:25):

And if you have good intent and you’re capable, you’re going to execute on a lot of things that don’t make sense. To Mickey’s point, for everybody who’s watching right now, it doesn’t make a whole lot of sense to meet somebody 20 minutes in and start talking about opening up offices, but it genuinely felt right. And I think to sit here all these years later and talk about that becoming a reality, those are the kind of stories that I hope inspire people who are listening not to be delusional and full of crap and think this is… I always worry about people thinking it’s the Secret, you just say it and it happens. There’s a lot more that goes into it than that.


Matt (08:09):

It seems like in a lot of ways, you had a secret, or at least you were an insider in some ways, Gary. Because I mean, you and I met in Omaha, Nebraska, where you were speaking on a stage in front of I want to say it was 300, certainly less than 500 people. And Jeff Slibowski, founder of Silicon Prairie News is the reason I was there. He’s also the reason I think you were there.


Matt (08:32):

And the fact that you would fly to the middle of the country when you live in the New York City area, you’re probably flying to the West Coast quite a bit with your wine business, to come and throw a wine party, to pour wine at a wine party at big Omaha, and just shut it down, it’s like you already knew there was a big opportunity in the middle of the country. And then here comes Mickey saying, “Hey, I want to ignite things and bring things to the Southeast.” What was it about the middle of the country that clicked for you and the opportunity beyond traditional tech hubs like New York or San Francisco, or even places like Austin?


Gary Vaynerchuck (09:20):

Common sense. I think humility and common sense, a lack of audacity, a belief in curiosity, an understanding of humanity, all those things play out. My high school years where I probably refined my business skills were I lived in Hunterdon County, New Jersey. And for those that don’t know, I mean, Hunterdon County, New Jersey makes Chattanooga and Omaha look like New York City. So I thought technology was omnipresent, and I understood that talent might be in the colleges or the neighborhoods of middle America or South, non-New York. By the way, at the time, New York wasn’t even respected as tech.


Matt (10:17):

Yeah, absolutely.


Gary Vaynerchuck (10:18):

It was [crosstalk 00:10:19]. So I didn’t think that people had calibrated yet that tech was oxygen, accessible, and that the reality would be that great companies would be built everywhere. And to me, even at that time, Facebook was a Boston company, with a kid from Connecticut. Pinterest was a Pennsylvania company. Did they happen to decide to move to SF because that’s where the development talent and the venture capital money at the time was? Yes.


Gary Vaynerchuck (10:54):

But I think coastal audacity is a humongous business vulnerability, and it was just not something I was interested in being a part of.


Matt (11:07):

Are there other advantages you guys think that having a company headquartered or having a headquarters in the middle of the country gives a company? Or even a tech professional who’s looking to plug into tech?


Gary Vaynerchuck (11:24):

I think there’s a million advantages. I mean, there’s cost advantages. Now, you’re going to start to see it go the other way. Now, I’m more interested in having employees anywhere and everywhere that allows me to mitigate my cost. I mean, when I asked Mickey to live in New York and work, it’s going to be a different… Nicky or [Spicky 00:11:48] or Sally are all going to think the same thing, which is, “What’s my cost of living against my salary, against what I want to do with money?” Whether that’s to invest or go on vacation.


Gary Vaynerchuck (11:58):

And obviously if your cost of living… I mean, Mickey and I even had this conversation. It was a lightweight, because I think we were just both long-term with each other, but there was an acknowledgement that, “Oh.” It was probably more like a high-five of, “Yeah.” I didn’t ask him to take less money. It was more like, “This is epic. You’re going to be able to have a much better quality of life in Chattanooga’s costs compared to Manhattan’s costs.”


Gary Vaynerchuck (12:21):

I think as we are now fully in an integrated Zoom and room kind of world, physical and virtual kind of world, the reality is that you’re going to start to see a lot of disruption. You already see it with what’s going on with humans and companies going to Puerto Rico, Miami, Austin. I mean, this is a very big moment in time of change.


Mickey Cloud (12:48):

And Chattanooga specifically, so I’m on the Executive Board of the Chamber of Commerce. I’m on a couple boards of non-profits that are about attracting talent and leveraging and building our entrepreneurial ecosystem here. And those are conversations that the minute the pandemic happened, and maybe probably by late April, May last year, we were having conversations around how do we attract people to Chattanooga now?


Mickey Cloud (13:14):

Because PC Magazine called Chattanooga the number one place to work from home, because we’ve got the fastest internet in the Western hemisphere here. We’ve got great quality life. It feels like a big small town, you can connect with people, and people want you to generally succeed here. And so, we’ve been on the offense trying to recruit companies, talent. And it’s a little bit of a different economic development game where it’s really easy to track like, “Hey, this company has an office here or moved its headquarters here. And that created 8,000 jobs.” It’s much more difficult to track three developers moved from Atlanta to Chattanooga to take advantage of this, but that’s the dirt work that still needs to be done.


Matt (14:05):

In terms of starting that office, I know culture is big to both of you. I would imagine that’s one potential risk of starting an office that’s not in the same location. How did you mitigate that risk as you branched out, started new hubs, and made sure that it still had that Vayner DNA?


Mickey Cloud (14:25):

So the strategy was we took 10 from our New York office. So we got recruited by Chattanooga to open the office here. It was essentially a group of entrepreneurs reached out to Gary and said, “I’ll buy.” Ted [Alling 00:14:40] was the main guy. He bought 2,500 copies of Jab, Jab, Jab, Right Hook, Gary’s I think third book. And in exchange, [inaudible 00:14:48] 24 hours to visit Chattanooga. And texted me on that trip saying, “Dude, I love Chattanooga.”


Mickey Cloud (14:54):

And we were talking about going to other markets. We were looking at Charlotte, Richmond, Raleigh, places like that. But I was like, “Well, I’ll go check it out.” I hadn’t been there since the 90s, but I had grown up going to camp. I knew it a little bit, but-


Gary Vaynerchuck (15:10):

By the way, that was the best part of the combo. I knew that intuitively, I felt something about Nooga, but I didn’t know if I could get Mickey to go there. And I remember that combo as well. I was like, “Mickey, Chattanooga?” And he’s like, “I went to baseball camp.” And I’m like, “That’s right. Some of the greatest memories of your life, right, boy?” That was a fun combo.


Mickey Cloud (15:35):

So, we made the decision summer/fall 2014 and then announced it at the holiday party in 2014. And that, “Hey, we’re going to open an office in Chattanooga.” At the time, we had New York and we had San Francisco and LA. So we were like, “All right, we’ve got the coasts covered. We’re going to open this off-the-coast office in Chattanooga, Tennessee and we want 10 of us to go from New York down to Chattanooga.”


Mickey Cloud (15:57):

And so at that point, I had people coming up to me at the holiday party saying, “Hey, when can we grab coffee? I want to talk to you about it.” Because some of the folks that we brought down, a lot of them, some of them maybe came from the Southeast, but a lot of them were just like, “Hey, this sounds like a great career opportunity and a fun thing to do to be part of a founding team of an office.”


Mickey Cloud (16:15):

And so, we ended up bringing 10 people down and then have hired local talent around that 10 to grow the office. So for that, that was a key strategy for a lot of our offices, Gary, whether in the US, globally. And so, it was certainly a way to make sure we had the DNA transported from New York and the headquarters to this office. And then it was about making sure that people knew that there could be connections.


Mickey Cloud (16:43):

So Gary comes down in Chattanooga pre-pandemic a couple of times a year, and other people from the New York office that would come down and visit and make sure that there was still that connection.


Matt (16:55):

Were there any uncertainties, or did you have any fear about starting this office in the middle of the country, that wasn’t one of the traditional top three, LA, SF, New York, cities for an agency like Vayner or Miami, even? Whether that was from you or your leadership team? I’m just curious if there was some early pushback before you saw all this momentum and traction, Gary?


Gary Vaynerchuck (17:23):

That’s the beauty of not having a board, or being publicly traded. I live and die in my decisions. So, no, I believed in it, I believe in it, and I’m sure there was whispers behind my back. But that’s par for the course. I don’t recall anything being too extraordinary pushback. Mickey?


Matt (17:57):

Was there anything that surprised you about starting a Chattanooga office that you didn’t expect?


Gary Vaynerchuck (18:05):

I don’t go in with expectations, Matt, in general, I think it’s one of my great strengths. I think a lot of things played out the way I thought. I thought Mickey would be an incredible candidate for mayor of the town. I knew his personality. I knew his disposition.


Gary Vaynerchuck (18:22):

I felt he was the right man for the job. That played out the way I thought. I’m trying to think if there’s anything. Not necessarily, not anything that I can really, really think of. Maybe the fact that I wanted a direct flight situation quicker and easier, but no, it’s an incredible community. I would probably say I’m surprised we don’t have more. I would’ve lost that bet.


Gary Vaynerchuck (18:59):

I always thought about Wichita and Des Moines. I think so much has started happening in a million different ways that we didn’t end up having Louisville. I think Mickey, we had a quick convo on it at one point. We didn’t really get to more satellites yet, and now, what does that even mean? But other than that, not really.


Mickey Cloud (19:25):

Well, and you [crosstalk 00:19:26]-


Matt (19:25):

No, go ahead.


Mickey Cloud (19:28):

I was going to say, one of the interesting parts of the evolution of the Chattanooga office in the past five years, six years has been the fact that when we opened, we were a satellite office of VaynerMedia, but VaynerMedia is a full-service advertising agency where works with some of the biggest brands in the world. And Chattanooga was definitely not like you’re going there for a client. We were going there because this community attracted us, and because there was entrepreneurs here that we believed in and we felt like we could have an impact on the entrepreneurial ecosystem here.


Mickey Cloud (20:00):

We weren’t going here for a specific client. We had some clients in the area, two-hour drive to Knoxville, Atlanta. So we had some clients, and then we were able to build from there. But we were targeting larger companies in the Southeast, Dallas, Florida, places like that that we were trying to work with bigger companies, because that’s how the business model worked. But about a year or two years in of people coming up and saying, I’d get a coffee meeting with someone. And they’d say, “Our budget’s $50,000 for marketing for the year. What can you do for me?”


Mickey Cloud (20:34):

And I said, “Nothing. I’m sorry, we don’t have an offering at that level.” And after about a year of that, two years of that, me and Jesse and a few of the people here went to Gary and said, “We got to start selling something.” And so we started doing some things on our own where we would do trainings, or we would go and meet and do some auditing and consulting and things like that.


Mickey Cloud (20:54):

And the VaynerMedia COO, James Arcini at the time noticed some of those things and helped guide us on as he was thinking about pulling together an offering with Gary for entrepreneurs, growth stage companies, challenger brands, the true middle market and below, it made sense for Chattanooga to be a part of that. Because we were having so many business development conversations here locally, regionally, where we were leaving money on the table because we didn’t have an offering to support a $250,000 budget.


Mickey Cloud (21:25):

And that was part of starting the Sasha Group, was we need to be able to support that size of company, and it doesn’t really fit in VaynerMedia’s halls at the size and scale that VaynerMedia was at, at that time.


Gary Vaynerchuck (21:42):

Exactly right.


Matt (21:44):

Gary, where did the name Sasha Group come from, and why is it important to you?


Gary Vaynerchuck (21:48):

Well, it’s named after my dad. His name’s Sasha, good Russian name. Needed a name, feel like my small business… Mickey can tell you, I’m a businessman. And so that makes me different in meetings, and Mickey has seen me with the biggest brands in the world and the biggest titans in business and with the smallest of small businesses.


Gary Vaynerchuck (22:16):

And I’d like to think, I don’t want to lead the witness, but my flexibility is high because it’s how I’ve built my career. I can really chameleon every room. I’m just as comfortable talking to Sal about his one pizza shop in the suburbs of Detroit as I am with Mark Benioff about Salesforce. I just really do believe I have that range and I’m humbled and flattered and excited to. I do think that the SMB part has a little even extra flare for me, because the impact is so extraordinary.


Gary Vaynerchuck (22:53):

One meeting with an SMB and giving them one good idea can really change a lot for them. And so, I learned my SMB chops in my dad’s liquor store, where I did have a great impact. And I lived the hyperbole. I lived a business that was doing less than $4 million a year in revenue, which is a big small business. But without any VC money, and even without the benefit of having a credit line, I was able to explode that business in a very short period of time based on my macro hypothesis, which is if you do the best behavior of the second, if you’re the best of the thing of this second, you get disproportionate returns on those investments from a marketing or operational or product offering standpoint. And so, I named it after my dad.


Gary Vaynerchuck (23:49):

And the best part of that story is when I told my dad. His reaction was negative because my dad is a very cynical old Russian dude. And I think for the first couple hours, he was trying to figure out what the angle was and what was the downside risk. A few weeks later, he was proud. I think he’s happy now, but yeah. That’s why we named it that way, and it’s been a really, really fruitful endeavor. It feels fun. The impact’s extraordinary. I think about some of the stuff we’ve worked on. You’re changing people’s lives.


Matt (24:24):

Well, and I love your fingerprints are all over that, right, Gary? And the fact that you bring the positivity, while maybe your dad is naturally pessimistic, it seems like you’re naturally optimistic, not unaware of potential downside, but overall optimistic about the opportunity.


Matt (24:43):

And I’m curious before you go here, what do you think is the big opportunity for the Unvalley? What kind of predictions would you make over the next five, 10 years for non-traditional tech hubs?


Gary Vaynerchuck (24:56):

Well, I mean, I think we’re going into the golden era. If you’re in the Unvalley right now, you need to go ham and explain to people, “Why not live here? Here’s a better tax situation. Look at all the yard you get for this price. Look how much the restaurants cost here. Look how epic the people are.” And oh, by the way, I mean, I’ve had the best business year of my life professionally.


Gary Vaynerchuck (25:25):

I could have been anywhere in the world. I haven’t left my home. Now, things will go back to… We’re not going to be in a global pandemic forever, thank God. But my behavior has changed. I don’t need to get on a plane for one meeting in Chicago, get that crappy 6:00 AM Chicago flight that I have to wake up at 4:30 for, to have a meeting and then fly back and get home.


Gary Vaynerchuck (25:54):

That’s a one-hour meeting on Zoom now that even a 63-year-old corporate America executive is signed up for. The cat’s out of the bag. If the Unvalley doesn’t capitalize in this decade, then they need to temper their expectations.


Matt (26:19):

I love that prediction and I’m with you 100%. I think we’re just at the beginning of the inflection point. And I know you’ve been predicting this for years, and predicted the exact target exit to Salesforce. I remember seeing that back in the day before that even happened in 2013.


Matt (26:37):

I know I met you in Omaha, Nebraska of all places, and I know you took time out of your day first thing in the morning this morning to be here with us. So Gary, I want to thank you for being here and sharing some of the Vayner story with us.


Gary Vaynerchuck (26:50):

I’m happy to be here. I’m glad to be a part of it. Great to see everybody. We’ll talk soon. Bye-bye.


Matt (26:53):

Good to see you, Gary. Thanks so much.


Matt (26:57):

Thanks for joining us gang, and for Building While Flying with the Sasha Group today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight.


Matt (27:09):

If you’d like to hear more about how business owners and brands are navigating these times, tune into the next episode. And if you’re so kind, please rate and review us. Plus, we love feedback, so let us know what you think, what you’d like us to dig into next on Building While Flying, across brands, businesses, marketing, and more.


Katie Hankinson (27:23):

Original music by Fulton Street Music Group.

Welcome to Building While Flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.


Earlier this year, Mickey and Gary joined Matt Hunckler for the Powderkeg Unvalley Conference. Powderkeg is a network of local communities with global reach for tech entrepreneurs, investors, and top talent. Unvalley is a two-day virtual event that explores the untapped potential beyond Silicon Valley. 


In this special bonus episode, we’re bringing their keynote session to our listeners, so you all can learn more about how The Sasha Group landed in Chattanooga, attracting talent in new cities, the value of community, and much more—directly from Mickey and Gary themselves.

In this special bonus episode, you’ll hear Mickey and Gary discuss:

  • How Mickey met Gary
  • Trusting your intuition
  • How VaynerMedia was recruited to come to Chattanooga 
  • Building a team for a new office hub while maintaining Vayner culture
  • The birth of The Sasha Group in 2019
  • Adapting business offerings to meet market needs 
  • Building the Vayner/Sasha brand in a new, mid-sized market
  • …and a whole lot more. 

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