Bootstrapped: a Podcast by the Dingman Center for Entrepreneurship

BootstrappedThe Dingman Center for Entrepreneurship produces Bootstrapped, a podcast featuring founders, investors and serial entrepreneurs. While the podcast covers many aspects of startup life, the heart of the show focuses on funding from both the founder and investor perspectives, thus the name Bootstrapped. The podcast is hosted by Holly DeArmond, managing director of the Dingman Center, and Joe Bailey, associate research professor at the Smith School. Each episode starts with trend stories from the hosts, then moves on to an interview with a special guest. Topics range from fundraising and marketing to team formation and customer acquisition.

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Co-Hosts

Holly DeArmondHolly DeArmond, Managing Director, Dingman Center for Entrepreneurship

Holly DeArmond, MBA '17 joined the Dingman Center in September 2012 as Assistant Director, Events and Marketing. In 2014, DeArmond was named associate director of the center and in 2019 she was named managing director. Holly's primary focus is leading the Dingman Center in support of its mission to build a community that discovers, equips, connects and celebrates entrepreneurs. Key responsibilities include oversight of center operations; venture programs; brand positioning; and external relations. DeArmond also develops and maintains relationships with donors, board members, EIRs, the Smith School community and other campus and regional partners.

Joseph BaileyJoe Bailey, Associate Research Professor, Robert H. Smith School of Business

Joe Bailey's research and teaching interests span issues in telecommunications, economics, and public policy with an emphasis on the economics of the Internet. This area includes an identification of the existing public policies, technologies, and market opportunities that promote the benefits of interoperability. Bailey is currently studying issues related to the economics of electronic commerce and how the Internet changes competition and supply chain management.

Past Co-hosts

Elana Fine, former Executive Director, Dingman Center for Entrepreneurship


Episode 53: Turning Passion for Politics Into a Thriving Business

Special Guest: Andy Shallal, MBA ’19, Founder & CEO, Busboys and Poets.

Andy ShallalOn this episode of Bootstrapped, we interviewed Andy Shallal, MBA ’19, founder and CEO of Busboys and Poets. Shallal founded the iconic restaurant chain in 2005, where it started from a restaurant/events venue/coffee shop/bar/bookstore in D.C. and expanded to eight locations today across the DMV. After years of operating his business, Shallal returned to school through Maryland Smith’s Executive MBA program, where he has acquired newfound tools to help his empire soar. Shallal sits down with the Bootstrapped hosts to discuss his motivations for starting Busboys and Poets, how his passion for democracy became the bedrock of the business, and the challenges he’s faced in building Busboys and Poets to what is is today and what it can soon become.

Season 7

Episode 53: Turning Passion for Politics Into a Thriving Business
Special Guest: Andy Shallal, MBA ’19, Founder & CEO, Busboys and Poets


Season 6

Episode 52: An Airline Pilot Turned Entrepreneur
Special Guest: Pramod Raheja '91, CEO & Co-Founder, Airgility, Inc.

Episode 51: From Brothers to Co-Founders: Building Businesses with Family
Special Guest: Zeki Mokhtarzada '00, Co-Founder, TrueBill, Inc.

Episode 50: From Founder to Funder: An Entrepreneur's Transition to Investing
Special guest: Bill Boyle '81, Founder, FiberGate, Inc.


Season 5

Episode 49: Building Diversity, Inclusion and Empowerment into your Brand Identity
Special guests: Jasmine Snead '17, MPH '19, MBA '21, CFO, Aurora Tights & Imani Rickerby '17, COO, Aurora Tights

Episode 48: From Touchdowns to Startups: Lessons on Success, Failure, and Investing from an NFL Star
Special guest: Santana Moss, Radio and Television Host

Episode 47: Flipping the Mental Switch from Entrepreneur to CEO
Special guest: Jay Sunny Bajaj '99, Founder & CEO, DMI

Episode 46: From Doctor to Entrepreneur: Launching a Recruiting Service for Caregivers
Special guest: Dr. Charlene Brown, Founder & CEO, Caregiver Jobs Now (formerly ReciproCare Jobs)

Episode 45: Bootstrapping a Green Cleaning Solution for Smelly Sports Gear
Special Guest: Stephen Steinberg '10, Founder & CEO, Raw Athletics


Season 4

Episode 44: Lessons on E-commerce and Pivoting from a Y Combinator Alumnus
Special Guest: Daniel Sugarman '12, Co-founder & CEO, Zentail

Episode 43: Going Green: Bolstering Your Brand With Social Activism
Special Guest: Scott Nash, Founder & Owner, MOM’s Organic Market

Episode 42: From Broadcasting to Podcasting: How to Leverage Unfair Advantages
Special Guest: Oscar Zeballos, MBA '16, Co-Founder of Podcast Village & Executive Producer of Bootstrapped

Episode 41: From Bootstrapped to Series D in Seven Years with EverFi
Special Guest: Jon Chapman, MBA '07, Co-Founder & President, EverFi

Episode 40: Applying a Business First Approach to Social Venture
Special Guest: Melissa Bradley, Managing Director, Project 500

Episode 39: Managing Public-Private Partnerships as an Entrepreneur
Special Guest: Eddie Inlow, MBA '09, Founder & CEO, Shift Transit

Episode 38: Developing a Sustainable Social Venture
Special Guests: Pam Rothenberg, Partner, Womble Bond Dickinson & Chris Finlay, Founder & Chairman, Shelters to Shutters

Episode 37: Gaming For Grades: Finding Success as Founders and Funders
Special Guests: Josh Goldberg '03 and Vadim Polikov, Co-Founders, Legends of Learning


Season 3

Episode 36: Maximizing Your Marketing on a Startup Budget
Special Guest: Hillary Berman, MBA '03 Founder, Popcorn & Ice Cream

Episode 35: Waste Not Want Not: The Importance of Adaptability
Special Guest: Jason Gates '11, Founder & CEO, Compology

Episode 34: Monetizing the Social Gaming Industry
Special Guest: Paul Capriolo '06, Entrepreneur-in-Residence, Dingman Center for Entrepreneurship

Episode 33: Guts, Grit and Gifts: Finding a Niche in Digital Marketing
Special Guest: Jignesh Shah, MBA '05, Co-founder & CEO, Rybbon

Episode 32: Building Your Own Luck as an Entrepreneur
Special Guest: Jennifer Lee-Harrison, MBA '12, Founder, Perfect Hair International

Episode 31: A Serial Entrepreneur’s Adventures in Cybersecurity
Special Guest: John Czupak '89, President & CEO, ThreatQuotient

Episode 30: Seasoned CEO Turned Silicon Valley Investor
Special Guest: Gary Swart '83, General Partner, Polaris Partners

Episode 29: A Personalized Approach to Investing
Special Guest: Kathryn Stewart, Managing Director, Cranbrook Capital

Episode 28: Streamlining Customer Experiences and Saving Pet Lives
Special Guest: Mark Olcott, MBA '13, Co-Founder and CEO, VitusVet


Season 2

Episode 27: Getting Social Media Users to Give Back
Special Guest: Dale Pfeifer, Founder & CEO, Goodworld

Episode 26: The Ins & Outs of Food Startups
Special Guest: Jason Cohen '96, Founder & CEO, Halen Brands

Episode 25: How to Navigate Disruptions in Retail
Special Guest: Brian Taff '89, President & COO, Streetsense

Episode 24: Investment Criteria from an NFL Superstar Turned Angel Investor
Special Guest: Domonique Foxworth, Senior Writer of The Undefeated, Co-Host on The Morning Roast on ESPN

Episode 23: Finding Funding and the Unlikely Customers
Special Guests: Matt Furstenburg '12 & Chanda Arya '10, PhD '14, Co-Founders, Grip Boost

Episode 22: Finding a Niche in a Crowded Market
Special Guest: Ursula Mead, Founder & CEO, InHerSight

Episode 21: Making Customer Acquisition an Easy Sell
Special Guest: Elise Whang, CEO & Co-Founder of SnobSwap

Episode 20: Not Getting Customers? Try Asking Why.
Special Guest: Bob London '83, CEO & Founder, Chief Listening Officers

Episode 19: Nervous About Your Elevator Pitch? Don't Sweat It
Special Guest: Glen Hellman, CEO & Founder, Driven Forward LLC

Episode 18: How to Monetize When Everything is Free
Special Guest: Aviva Goldfarb, Founder, The Six O’Clock Scramble

Episode 17: Computer Science Background Not Required
Special Guest: Brad Sayler, Co-founder and CFO/COO of Spotluck

Episode 16: Social Venture MISFIT Juicery on Leveraging Your Social Capital
Special Guests: Ann Yang, Co-Founder, MISFIT Juicery & Phil Wong, Co-Founder, MISFIT Juicery


Season 1

Episode 15: From T-shirts to Crowdsourcing: Launching Two Very Different Ventures
Special Guest: Micha Weinblatt '05, Founder of Crooked Monkey and Betterific

Episode 14: Understanding Equity: What Entrepreneurs Should Know
Special Guest: Andrew Sherman, Partner at Seyfarth Shaw, LLP and Adjunct Professor, Smith School of Business

Episode 13: How to Monetize Your Startup
Special Guest: Ed Barrientos, CEO, Brazen

Episode 12: Put Your Social Media Skills to Work
Special Guest: Ali von Paris '12, Founder, Route One Apparel

Episode 11: Tien Wong Discusses Real Estate Finance and His Journey from Founder to Angel Investor
Special Guest: Tien Wong, CEO of Tech 2000 & Founder of CONNECTpreneur

Episode 10: Coffee Talk with the JavaZen Co-founders: Building a Lifestyle Brand
Special Guests: Eric Golman '15, Co-founder & Chief Energy Officer, JavaZen
Ryan Schueler '15, Co-founder & Chief Relationship Officer, JavaZen

Episode 9: Follow Her Lead: Amy Millman as a Pioneer for Women in Business
Special Guest: Amy Millman, President, Springboard Enterprises

Episode 8: Taking a Startup from the Dorm Room to Shark Tank
Special Guest: Evan Lutz '14, Founder, Hungry Harvest

Episode 7: A Serial Entrepreneur and Angel Investor Talks Exits and Investing
Special Guest: Jason Shrensky, Founder, CEO of Complex Interests

Episode 6: Startup Snags Success with Hotels.com for Boaters
Special Guests: Dan Cowens, MBA '14, Founder, Oasis Marinas and Snag-a-Slip.com
Paige Holden, MBA '14 VP of Marketing & Communications, Oasis Marinas and Snag-a-Slip.com

Episode 5: Can Entrepreneurship Be Elegant?
Special Guests: Danielle Tate, Founder & CEO, MissNowMrs.com
Culin Tate, Co-Founder & VP, MissNowMrs.com

Episode 4: Startup Marketing: Betas. Pilots. Customers.
Special Guest: Liz Sara '80, Founder, Best Marketing, LLC

Episode 3: Crowdfunding a Cat Café
Special Guest: Kanchan Singh '12, Founder, Crumbs & Whiskers

Episode 2: Parking & Technology Collide
Special Guest: Sam Medile '80, CEO, Unified Parking Partners/Angel Investor

Episode 1: Government Funding for Startups: A Best Kept Secret
Special Guest: Mark Walsh, Chief Investment & Innovation Officer for the U.S. Small Business Association