Dingman Bootstrapped

On 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 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.

On this episode of Bootstrapped, we interviewed University of Maryland alumnus Pramod Raheja '91, co-founder and CEO of Airgility and mystaffNOW. Since graduating from Maryland, Pramod navigated a split career as an Airline Captain for United Airlines and also as a serial entrepreneur. Now as the CEO of Airgility, Pramod has been able to leverage his experience as an entrepreneur and as an alumnus at UMD to bring his passion for aerospace engineering to life. On this episode, Pramod shares his experience combining his love of the aerospace industry and entrepreneurship, and how he’s been able to maintain his passion for flight at the center of it all.

On this episode of Bootstrapped, we interviewed University of Maryland alumnus Zeki Mokhtarzada '00, co-founder of TrueBill and formerly of Webs. After graduating from Maryland, Zeki was ready for a life of entrepreneurship and he knew exactly where to find co-founders.  Alongside his brothers, Zeki co-founded Webs, one of the earliest free web hosts. Together, Zeki and his brothers led Webs to an acquisition to Vistaprint in 2011, and they’ve since gone on to found TrueBill, a company dedicated to tracking and managing all of your finances in one place. On this episode, Zeki shares his experiences balancing family and business, as well as leading a team focused on innovation.

On the season 6 premiere of Bootstrapped, host Joe Bailey and new co-host Holly DeArmond, MBA '17, managing director of the Dingman Center, interviewed University of Maryland alumnus Bill Boyle ’81. Bill is the founder of FiberGate, Inc, chairman of the Dingman Center’s Board of Advisors and an active member of the Dingman Center Angels. From Fiber Optics to the funding table, Bill Boyle has leveraged his experience building and running his own venture into a successful career as an angel investor and venture mentor to numerous students. On this episode, Bill shares his experience running FiberGate for 17 years until its successful exit, and provides a firsthand account of his journey into the world of advising and angel investing.

On this episode of Bootstrapped, we interviewed current University of Maryland student Jasmine Snead ’19 and alumna Imani Rickerby ’17, co-founders of 2019 Pitch Dingman Competition finalist startup Aurora Tights. As both women of color and figure skaters, Jasmine and Imani struggled to find tights that matched their skin tone, and saw their performance and confidence suffer as a result. To solve this problem, in college they started Aurora Tights, an athletic brand that designs performance sports gear in an array of tones for all complexions and sizes. On this episode, Jasmine and Imani share how they explored consumer interest, navigated contract manufacturing and formed a diverse team to help all women feel comfortable in their skin.

On this episode of Bootstrapped, we interviewed Radio & Television host Santana Moss. Moss played in the NFL for fourteen seasons. As the first-round pick in the 2001 NFL draft, Santana knew that he was going to need to take proactive measures to maintain his newly acquired wealth. Santana adopted a live and learn approach to entrepreneurship and began investing in real estate and other small businesses. All with varying degrees of success. From his early missteps, he gradually learned what to look for in an investment. On this episode, Santana shares how he learned the hard way that you shouldn’t blindly trust everyone you come across and the importance of perseverance following failure.

On this episode of Bootstrapped, we interviewed alumnus Jay Sunny Bajaj ’99, the Founder and CEO of DMI and a Robert H. Smith School of Business advisory board member. Growing up with two entrepreneurs as parents, Sunny knew he was going to have his own business one day. Now, Sunny operates a $350 million company that offers comprehensive digital solutions to federal and commercial markets. On this episode, Sunny discusses how he stayed close to innovation to win contracts in the federal market space, and how he shifted his mindset from entrepreneur to CEO to grow as a leader alongside his business.

Listen to Dr. Charlene Brown’s story of starting CareGiver Jobs Now (formerly Reciprocare Jobs), a recruiting platform to help caregivers find jobs in the healthcare industry. She shares the challenges of balancing a two-sided market and navigating product market fit.

As a student hockey player at University of Maryland, startup founder Stephen Steinberg developed a powerful yet safe-on-skin cleaning solution for his smelly sports gear. Learn how he bootstrapped his company, Raw Athletics, which sells green cleaning products to gyms, athletic teams and consumers all over the country.

On this episode of Bootstrapped, we interviewed UMD alumnus and co-founder and CEO of Zentail Daniel Sugarman ’10. Daniel and his co-founder, Daniel Sperling-Horowitz, first launched a business called HD Trade Services that used technology to decrease fraud in international trading. After entering Y Combinator, they ultimately realized their business model was not sustainable, pivoted, and renamed themselves Zentail to offer their strong automation and data analytics software to retailers. Today, Zentail is an ecommerce platform that gives online retailers and brands the ability to sync catalog and inventory data, maintain competitive pricing, obtain analytics and ship products through channels such as Amazon, Jet.com and Walmart. In this episode, Daniel shares how forming a network and understanding the capital structure behind his startup allowed him to pivot his idea to a different runway while leveraging his current strengths.