The Entrepreneur’s Studio

In the world of technology, there is often a prevailing mindset that, ‘if it can exist, then it should exist.’ But according to serial entrepreneur and tech pioneer Caterina Fake, this may not always be the case. As a maverick in her industry, Caterina asks the question, “Should this exist?” And if so, what is our ethical responsibility for making it available to the world? 

Caterina Fake is known for co-founding the ground-breaking photo sharing platform Flickr as well as having played a pivotal role in the development of foundational AI algorithms through her company, Hunch. 

As a member of Yes VC Venture Capital Firm, Caterina invests in pre-seed and seed stage companies, making a significant impact on the entrepreneurial landscape.

In today’s episode Caterina joins us in-studio to share some of the early stories that shaped her career, mindsets that guide her creative ventures and her unique insights into the future and ethics of technology.

• How Art, Technology & Community intersect
• The importance of sharing ideas 
• Caution and Excitement of where AI is headed

Learn More about Caterina Fake

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Oklahoma City’s ”East Side" had been a social and economic center for African American life but through gentrification and neglect, the area became a marginalized part of town. 

In 2016, Jonathan Dodson’s Pivot Project selected an abandoned strip mall on Northeast 23rd Street for what would ultimately become the EastPoint Project.

The development at Eastpoint gave activist and award-winning rapper Jabee Williams the opportunity to establish Eastside Pizza House alongside other black business owners in a thriving community atmosphere. 

In today’s episode, Jabee shares his story of going from entertainer to activist, preserving history and innovating new business models.    

• Creating positive change through creativity and collaboration.
• Honoring the past while innovating the future
• Advocating the under-served through community engagement 

Learn More about Jabee

Eastside Pizza House 

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The Entrepreneur’s Studio is powered by Heartland Payment Systems. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Developer Jonathan Dodson left his job as a corporate banker and followed his passion to revitalize Oklahoma City through urban infill and adaptive reuse of commercial property. 

His development group, Pivot is committed to creating ethical community development that is the product of public interest and addresses a community need.

In today’s episode, Jonathan shares his story about how he felt a moral imperative to invest in underserved communities and the challenges he faced in establishing what became an internationally recognized economic revolution.

Key Points: 

• The importance of ethical development principles
• The impact of gentrification
• Unorthodox funding methods and creative negotiations  

Pivot Project  

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Browse our library of conversations with successful entrepreneurs who have been in your shoes. 

The Entrepreneur’s Studio is powered by Heartland Payment Systems. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers. 

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Christina Tosi is a chef and the founder and CEO of Milk Bar, a unique bakery concept reinventing classics like cereal and birthday cake with plenty of imagination. Creativity is the spirit of Milk Bar and a throughline for everything Christina does, but it can be hard to run a business without some of the traditional, tried-and-true practices.

In this episode, Christina takes a deep dive into her creative process, business practices and the four core values which guide her to leading a successful enterprise. 

This is part 2 of our conversation with Christina Tosi. 

Key Points:

• Nurturing a creative mindset
• Streamlining operations 
• Learning how to bend the rules 

Connect with Christina Tosi

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The Entrepreneur’s Studio is powered by Heartland Payment Systems. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers. 

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Nostalgia was a key driver of Christina Tosi’s vision for Milk Bar. As it turns out, the masses share her sentiments. Whether your plan is to make childhood memories the theme of your business or a single item on your menu, Christina feels everyone can benefit by touching customers on a personal level.

Christina Tosi is the award-winning chef and founder of Milk Bar, a singular bakery concept that merges her love for down-to-earth, comforting baked treats, culinary expertise and unexpected, creative combinations. 

In this episode, Christina shares how she went from being a math major in college to a James Beard recipient, a TV personality and the founder of a bakery empire.

This is part 1 of our conversation with Christina Tosi. 

Key Points:

• Nostalgia as a key driver for entrepreneurial pursuits
• Gut instinct as a business guidepost 
• What it takes to build a business model that does not exist 

Connect with Christina Tosi

Read The Transcript 

Enjoy the podcast? Subscribe and leave a positive review on Apple podcasts.

The Entrepreneur’s Studio is powered by Heartland Payment Systems. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

In part one of our conversation with philanthropist Charles Best, we discussed the 3 Innovations of Crowdfunding, Digital Marketplace and Cause Marketing. In today’s concluding segment, we take a deep dive into some of the processes behind those innovations. 

We’ll find out what motivated Charles to choose the non-profit model, how he raised his operating Capital while still teaching high school and his unique method of value-based screening of potential team members. 

Key Points:

• Benefits of choosing the non-profit model 
• Value-based screening of potential team members. 
• The art and science of getting to yes when making a pitch to potential donors.  

Resources: 

DonorsChoose

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Book mention: ‘Drunk Tank Pink’ by Adam Alter.

This is part two of our conversation with Charles Best. Visit theentrepreneurs.studio and subscribe to the podcast for notifications and other exclusive content from The Entrepreneur’s Studio.

Credits:

The Entrepreneur’s Studio is powered by Heartland. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Charles Best is the founder of DonorsChoose, a nonprofit organization that connects teachers in need of classroom resources with donors who want to help.

Charles launched DonorsChoose in 2000 while teaching history at a Bronx high school. His efforts began as a local, independent passion project among peers but went on to be named one of the 50 most Innovative organizations in the world. 

Today, half of all the public schools in America have at least one teacher who has created a classroom project request on DonorsChoose.org, and more than 5 million people have donated, providing books, art supplies, technology and other resources to students in low-income communities.

In this episode, Charles shares the story of what motivated him to take on this philanthropic work as well as the unwavering determination that guided him from grassroots marketing techniques to gaining national attention from The New York Times, Newsweek and Oprah. 

Key Points:

• 3 Innovations of crowdfunding, digital marketplace and cause marketing
• The importance of correct branding from the start
• Increasing brand awareness through partnerships  

This is part one of our conversation with Charles Best. 

DonorsChoose

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The Entrepreneur’s Studio is powered by Heartland. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Showing up “on time” and “on brand” may look like an easy win from the outside, but underneath outward success is a long journey of perseverance and dedication. 

In this episode, fashion icon Rebecca Minkoff shares how she secures out-of-the-box partnerships, handles imposter syndrome and critical feedback, and believes it’s important to define success on your own terms. 

Key Points include:

• Separating yourself from your brand 
• The team sport of partnerships 
• Wins and losses in the hiring process 

This is part 2 of 2. 

Resources/Links: 

Rebecca Minkoff 

Transcript

The Entrepreneur’s Studio is powered by Heartland Payment Systems, providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Rebecca Minkoff is a fashion designer, podcast host, author and founder of The Female Founder Collective. Though she’s known far and wide for her namesake brand of clothing and accessories (including her uber-popular handbags), Rebecca’s entrepreneurial path was riddled with character-shaping challenges from the start. 

In this episode, Rebecca shares the story of how her hard work, persistence and creativity took her from humble brand beginnings through post-acquisition life today.

Key Points:

• Staying persistent through challenging times 
• Cultivating purposeful relationships
• The importance of handling negative feedback well.

Read The Transcript

This is part 1 of 2.

The Entrepreneur’s Studio is powered by Heartland Payment Systems. Providing nearly 1 million entrepreneurs with the technology to make money, move money, manage employees and engage customers.

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io 

Rachel Cope is the founder and CEO of 84 Hospitality Group. She is known for her innovative restaurant concepts and contribution to Oklahoma City’s budding food scene. Her flagship restaurant, Empire Slice House is a popular, New York style pizzeria with multiple locations across Oklahoma. 

In this episode, Rachel shares the creative beginnings of how Empire Slice House began and how the commitment to quality has sustained her across the years.

Follow The Entrepreneur’s Studio so you never miss an episode:

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The Entrepreneur’s Studio is sponsored by Auris, helping small and mid-sized businesses simplify payroll and HR with powerful tools and real human support. Learn more at https://www.auris.io