Building While Flying

The career world is not how it used to be. The idea of picking one job after college and sticking with it for a lifetime is no longer sustainable. Nor should it be. Having a community where you can learn new skills, familiarize yourself with tech, and get advice from others is priceless in today’s world. The rapid reskilling movement is the wave of the future, and we should all jump in.

Welcome to Building While Flying!

This weekly podcast is brought to you by the 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.

Ruben Harris wants everyone to have a space to learn new skills and build new careers.

As CEO of Career Karma, Ruben Harris sees the incredible need for reskilling. He describes Career Karma as “an alternative LinkedIn for blue-collar workers.” And with over 55 million Americans filing for unemployment since the pandemic hit, it’s a much-needed platform for those looking to reshape their careers moving forward.

It’s not hard to see how Ruben was able to see the gaps in online job platforms. With a career background as diverse as his, he was able to see the needs of those who may not be in the corporate ladder-climbing category. As an accomplished musician, former investment banker and startup enthusiast, Ruben noticed a trend. There was a gaping lack of platforms for those looking to reskill and shift directions in their career.

In this episode, Ruben enlightens Katie on the rapid reskilling movement and why it’s so incredibly essential at this moment in time. He shares his brilliant ideas for Reskill America: The Great Rehiring Initiative, a program dedicated to providing resources like laptops to communities that need them. And he gives us a bit of his background that gives context to his incredible passion for this type of work. Tune in, and then you can say you knew of Ruben back before his company were the category kings of the rapid reskilling movement.

Other in-flight topics:

• The diverse career background that gave birth to Career Karma
• What to expect when you join Career Karma
• The skill gaps in America
• The power of tech skills
• Ruben’s brilliant WW2 tie-in
• Reskill America
• Mickey’s thoughts in the Sasha Sidebar

Links:

Career Karma

Reskill America: The Great Rehiring Initiative - https://careerkarma.com/reskill-america/apply/

Announcements - https://www.crunchbase.com/funding_round/career-karma-series-a--c59b9d2a

As an entrepreneur, the world of social media marketing can seem incredibly overwhelming. When do you post? What do you say? How do you keep up with it without it conflicting with other business tasks? The key to effective social media marketing is authenticity, honesty and accountability.

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. 

Jasmine Star told her story authentically on social media, and people paid attention.

More than a decade ago, Jasmine Star decided to quit law school and pursue a career as a photographer. She had no idea what she was doing, but she shared the entire process on her blog and eventually her social media. People paid attention. She wasn’t sure of her abilities as a photographer, but she grew more confident with her ability to effectively market herself online. Today, Jasmine empowers entrepreneurs and businesses to do the same.

Social Curator, founded by Jasmine, is a monthly subscription service that gives businesses photos and templates to use on their social media platforms. This innovative service specializes in amplifying business creativity, sparkling conversations through social media and captivating ideal clients.

In this episode, Jasmine tells Katie all about the unique career journey that led to Social Curator. Jasmine passionately explains that it's not necessarily about being the best at what you do, but instead, it’s about being honest about what you do. That vulnerability and openness can connect with potential clients and customers in a way that no corporate ad could ever touch. Jasmine has learned so much through her own social media. She loves sharing her knowledge with entrepreneurs who may be a bit timid about the social marketing landscape. If Instagram, Twitter, Facebook and TikTok feel like another planet to you, time to tune in!

Other in-flight topics:

• Jasmine’s origin story
• Her journey with photography
• Why it doesn’t matter if you’re good at what you do or not
• The 3 main pressure points of social media marketing
• Managing business and marriage
• The Taylor Swift quote you need to hear
• Jasmine’s pre-flight checklist

Links:

Social Curator - https://socialcurator.com/

Jasmine’s Website - https://jasminestar.com/

Follow Social Curator on Instagram - https://www.instagram.com/socialcurators/?hl=en

Follow Jasmine on Instagram - https://www.instagram.com/jasminestar/?hl=en

Just because we’re living through the most tumultuous time in human history doesn’t mean we can’t still do some good. In fact, it’s all the more reason to. It’s so refreshing to see those that have seen success with startups give back to their communities.

Welcome to Building While Flying!

This weekly podcast is brought to you by the 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.

Ted Alling is doing so much good in Chattanooga.

A big part of the reason why there’s a VaynerX office in Chattanooga is Ted Alling. This guy has so much pride for his town, you can’t help but fall in love with it from his passion alone. As co-founder of Chattanooga Prep, he demonstrates this passion in the most admirable way. This school for boys prepares tomorrow’s entrepreneurs and leaders by giving them a strong, solid and loving foundation. 

Ted is the co-founder and former CEO of Access America, a $500 logistics startup company. Access America eventually merged with Coyote Logistics, a UPS subsidiary. So obviously, Ted is a perfect example of massive startup success. 

The driving force behind much of what Ted does is a desire to build Chattanooga into a destination for young businesses. This is why he helped co-found Lamp Post Group in 2010, a venture capital firm.  They have invested $36 million into the local entrepreneurial ecosystem, all in an effort to turn their beloved city into a landscape ripe for the entrepreneurs of tomorrow.

In this episode, Mickey and Ted, who happen to be close friends, chat all about startups and the good you’re able to do with their success. They discuss navigating personal relationships when they also involve business, and how Ted’s been able to beat the odds of mixing friendship with startups. Ted is such a caring, thoughtful guy. And it’s so amazing to hear all the work he’s doing with the boys’ prep school and the Chattanooga community as a whole. This is a feel-good episode for sure.

Other in-flight topics:

• Ted’s upbringing
• The early stages of his career
• Partnering with friends
• The challenges of logistics startups
• All things Chattanooga
• The reasons behind the prep school idea

Links:

Connect with Ted on LinkedIn -  https://www.linkedin.com/in/tedalling/

Dynamo Ventures - https://www.dynamo.vc/

Lamp Post Group - https://www.lamppostgroup.com/

Chattanooga Preparatory School - https://www.chattanoogaprep.com/

It wasn’t just the pandemic that shook things up in 2020. The civil unrest triggered by horrible racial injustices left emotions raw. In some ways, this rawness has allowed us to be less delicate when making business decisions that reflect specific values. Being fiercely unapologetic while changing the world, especially the business world, is 100% necessary.

Welcome to Building While Flying!

This weekly podcast is brought to you by the 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. 

Tai Beauchamp is fiercely unapologetic as an entrepreneur and in life.

As a recognizable media personality, public speaker, style authority and creative director, Tai Beauchamp is all about empowering women. No matter the medium, Tai’s purpose has always been clear. She wants to provide a space for women, especially women of color, to be inspired to contribute in every sector to the fullest of their abilities. Her first loves, beauty and fashion, were behind her early career as a magazine editor for publications like Harper’s Bazaar and Good Housekeeping. At 22 years old,  she was one of the first fashion and beauty editors at O, The Oprah Magazine. 

But above all, Tai is an entrepreneur. Her newest venture, BROWN GIRL Jane, co-founded along with sisters Malaika and Nia Jones, has already smashed expectations in a short nine months. This innovative company offers a line of Broad-Spectrum CBD products designed to “support the wholeness of our sisters through internal balance and external beauty”.

In this episode, Katie and Tai have a candid chat about powering through the uncertainty of the present while acknowledging the divides we still have to bridge. Tai, by her own account, has always approached business differently. But it’s that very difference that has led her to such a distinctly unique undertaking like BROWN GIRL Jane. Tai describes the instances and career experiences that have prepared her for this moment in time, and the challenges she’s faced thus far. She also spills some of the ingenious ideas she’s come up with for her new company. Ideas so brilliant that she was able to score partnerships with major brand names in a matter of days. This woman is a force, and her passion for not only creating successful businesses, but evoking systemic change while doing so, is incredibly inspiring. We promise you’re not going to want to miss this one.

Other in-flight topics:

• How Tai describes herself
• What it’s like to grow up surrounded by educators
• Tai’s amazing start to her career right out of college
• The opportunity to create new movements
• The Brown Girl Swap
• Being fiercely unapologetic
• What is most important and where can you maximize outcomes?
• Tai’s pre-flight checklist

Links:

Tai’s Website

Tai on Instagram

BROWN GIRL Jane

Tai’s TEDx Talk

Podcast: How I Built This (referenced by Tai) 

Over the last couple of decades, digital media and personal technology like smartphones, has completely changed the way we do business. This is true for marketing, for selling and for customer communication. And it’s even more true for the healthcare sector. So how do you continuously adapt without missing a beat? Listening, learning and never being afraid to pivot could be the key.

Welcome to Building While Flying!

This weekly podcast is brought to you by the 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. 

Gary Bisbee has been learning and listening throughout his entire career.

Gary Bisbee, Ph.D., is the Co-founder, Chairman and CEO of Think Medium. This innovative company provides personal insights to healthcare leaders. Gary’s vast career spans executive positions in healthcare organizations from Wall Street to academia. His passion for what he does is extremely evident and he prides himself on using his platform to inspire thoughtful leadership. Gary’s done a little bit of everything (including professional Opera singing!), and he is so amazing at articulating what he’s learned from each experience.

In this episode, Mickey asks Gary about lessons he’s learned about the healthcare industry during this incredibly volatile time. With steadiness and infinite wisdom, Gary imparts how crucial it is to listen and learn always. And he gives us plenty of examples and stories of how he’s done just that throughout his career, and throughout the pandemic. The healthcare sector may seem a bit foreign to us in other areas of business, but Gary’s insights remind us of the universal similarities. He is one cool cucumber, and it’s obvious from this conversation that we all can learn so much from each other. So take a minute to listen and learn with us.

Other in-flight topics:

• A brief explanation of Think Medium
• Gary’s super interesting backstory
• Gary’s thoughts on the “building while flying” metaphor
• Knowing when to hold em’ and when to fold em’
• Is pivoting a bad thing?
• Lessons of the healthcare world
• The power of convenience
• Data, data, data
• Learning and listening
• Why understanding how your customers learn is everything
• Gary’s pre-flight checklist

Links:

• Gary on LinkedIn
• Think Medium
• Fireside Chat (Gary’s Podcast)
• Book - n=1: How the Uniqueness of Each Individual Is Transforming Healthcare 

This pandemic has hit businesses across all sectors in different ways. But something we can all agree on is that brick and mortar retail stores have taken some of the biggest blows of all. Of course, resilience comes into play. But are there ways to adapt in such trying times? Can you come back from a setback of this size?

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. 

Ken Giddon wants shopping at Rothmans to be efficient and rewarding for his customers.

Rothmans Men Clothing is one of those archetypal New York landmarks that we all recognize when we’re in the city. As the owner of this cherished retail spot, Ken Giddon has seen his fair share of catastrophes. His store survived 9/11, Hurricane Sandy and the financial crash of 2008, so a pandemic is no big deal, right? Well, actually, according to Ken, nothing has compared to what he’s seen this last year. But that doesn’t mean the end for Rothmans. It’s quite the opposite.

In this episode, Ken gives us the incredible backstory of how Rothmans came to be. His grandfather’s advice, “We’re just selling pants,” is always at the forefront of Ken’s mind. This is entirely evident in his cool, calm, laid back approach to pretty much everything. He gives us the lowdown on the incredible ways he’s adapted the business during the pandemic. And he gives us some hints about the funky ideas he has for the future. Don’t let Ken’s zen persona fool you. His company had to close its doors and sit on millions of dollars worth of inventory when Covid hit. And, of course, there was that million-dollar NYC rent price tag to worry about. What he’s been able to do is no easy feat. This was such an uplifting conversation and Ken had some amazing insights. If you find yourself at a crossroads with your small business right now, you’re going to want to listen up.

Other in-flight topics:

Rothmans backstory

What it’s like to mix family and business

What’s so gritty about NYC

Weaving and bobbing

What makes the buying experience different at Rothmans

Negotiation during a pandemic

A Roth Truck?

Some hilarious advice our James Orsini gave Ken

Ken’s pre-flight checklist

Links:

Ken on LinkedIn

Rothman’s - https://www.rothmansny.com/ 

Customer behavior is changing. We’re not running to the store anymore to pick up milk after work, or popping in the gas station for a candy bar. Our office is at home, and our groceries get delivered. So how do businesses handle the ever-evolving customer behaviors of the pandemic? How do you adapt your eCommerce strategies to not only cope with the times, but thrive?

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. 

Rachel Tipograph has been kicking a** in the industry since her early 20s.

As CEO and founder of the enterprising and marketing eCommerce platform MikMak, Rachel has watched customer trends like a hawk. In fact, she always has. Rachel started her career thinking she’d become a Hollywood agent, and even had a stint as an intern at SNL. But her entrepreneurial streak and flair for commerce led her a different direction. Long story short, Rachel ended up at GAP, increasing their profits by 70% and knocking a decade off their average customer age. She did all this at 22 years old.

This savvy spirit and keen eye led to the creation of MikMak at a pivotal time for eCommerce. She eventually had to do quite the pivot herself, and revamped her entire business model. The big guy, our very own Gary Vaynerchuk, was one of her investors. His confidence in her and her plan helped make that risky pivot possible, and it paid off big time. MikMak is now one of the fastest growing companies in America.

In this episode, recorded near the end of 2020, Rachel breaks down how the pandemic has completely shifted customer attitudes and behaviors. She tells us what people are buying now that they haven’t bought for decades. And she explains how she accumulates and tracks that data and how you use those same trends to adapt your current business model. She also lays ways she’s adjusted to a fully remote workforce while keeping everyone motivated and seen. This leader knows her stuff. No wonder Goldman Sachs named her one of “The 100 Most Intriguing Entrepreneurs.” We were intrigued indeed, and this flight was a fun one.

Other in-flight topics:

• The many lists Rachel’s been featured on
• How Rachel transformed Gap
• Why corporate America isn’t so bad
• 2020 Consumer Demand
• How to know where to spend your media dollars
• Replenish, replenish, replenish
• Nostalgic buying
• Rachel’s hilarious meeting with Gary
• Rachel’s podcast Brave Commerce
• What’s on Rachel’s Pilot Checklist
• Two Words: PIZZA TIME

Links:

Rachel on Instagram - @racheltipograph

Rachel on LinkedIn - racheltipograph

MikMak - https://www.mikmak.com/ 

Brave Commerce Podcast - https://www.mikmak.com/brave-commerce-podcast 

Pizzatime - Arrange a pizza party for your remote team! https://www.pizzatime.xyz/ 

The Sasha Group is the small to midsize business arm of the VaynerX family of companies. Through strategy, branding marketing, and media, we help ambitious companies build strong brands that flex with the times. 
Right now, those times are full of volatility and ambiguity. And businesses and brands are having to shift and adapt. Across all sectors, there is an air of experimentation: brands are trying new things, testing and learning, and “building the plane while flying.”
Building While Flying is a new, biweekly podcast from The Sasha Group that will tackle uncertain times by adopting an uncertainty mindset - we can’t predict the future, but we can listen, learn, apply and share as we all navigate complex times together. We’ll be speaking to a diverse range of business leaders and founders about how they tackle challenges, stay resilient and grow - with real life examples of how these strategies have been put into practice.