Small Business Playbook
Online⎮May 2, 2024

Small Business Playbook

New Strategies to Elevate Your Business in 2024

As small business leaders chart the course for their organizations, it’s essential to focus on issues that are sometimes out of their control, such as the ever-changing economic landscape, emerging technologies and the pace of adaptation, and of course, an upcoming election that could impact policies and regulations for businesses of all sizes.

Staying one step ahead on these matters is critical to success. CNBC’s Small Business Playbook will convene some of the top experts in entrepreneurship to offer valuable insight and advice to help small businesses across all sectors succeed in the short-term and long-term.

For CNBC Small Business Playbook editorial coverage, stories and video, visit


Harley Finkelstein

Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley completed his law degree as well as his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Harley is an Advisor to Felicis Ventures, and one of the “Dragons” on CBC’s Next Gen Den. He received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, Fortune’s 40 Under 40, and was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the Board of Directors of the C100, and from 2017 to 2020 he was on to the Board of Directors of the Canadian Broadcasting Corporation (CBC). He is currently on the Board of Operation Hope, a non-profit providing financial literacy empowerment and economic education. Harley starred on Discovery Channel’s I Quit, and recently co-founded Firebelly, a modern high-end tea brand.

Gary Vaynerchuk

Gary Vaynerchuk is the chairman of VaynerX, a modern-day media and communications holding company and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s 4 locations.

In addition to VaynerMedia, VaynerX also includes Gallery Media Group, which houses women’s lifestyle brand PureWow and men’s lifestyle brand ONE37pm. In addition to running VaynerMedia, Gary also serves as a partner in the athlete representation agency VaynerSports, cannabis-focused branding and marketing agency Green Street and restaurant reservations app Resy.

Gary is a board/advisory member of Ad Council and Pencils of Promise, and is a longtime Well Member of Charity:Water.

Gary is a highly sought after public speaker, a 5-time New York Times bestselling author, as well as a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, and Uber.

Gary is currently the subject of DailyVee, an online documentary series highlighting what it’s like to be a CEO and public figure in today’s digital world, as well the host of The GaryVee Audio Experience, a top 100 global podcast, and host of #AskGaryVee, a business and advice Q&A show which can be found on both YouTube and Facebook.

Gary also appeared as judge in Apple’s first original series “Planet of the Apps” alongside Gwyneth Paltrow, Jessica Alba and

Elena Delle Donne

Elena Delle Donne is one of the most dynamic professional basketball players in the history of women’s basketball. On the court, she shines with her confidence and complete game. Off the court, Elena is a family woman, dedicated wife, philanthropist, and outdoor lover.

Born and raised in Wilmington, Delaware, Elena has always held a strong sense of herself and possessed a spirited love for her family. Growing up, she played a variety of sports but ultimately found a love for basketball. She chose to play at the University of Delaware to stay close to home. In her freshman season at Delaware, she was named the Colonial Athletic Associations’ Player of the Year and Rookie of the Year.

Her brilliance continued as Elena was drafted 2nd overall by the Chicago Sky in the 2013 WNBA Draft. After an explosive first season, she was crowned the 2013 Rookie of the Year. She continued her dominance and is a six-time WNBA All-Star (2013, 2014, 2015, 2017, 2018, 2019), WNBA Scoring Campion (2015), a two-time Most Valuable Player (2015, 2019), and a WNBA Champion with the Washington Mystics (2019).

Off-court, Elena is one of the most marketable women’s athletes. Her key partnerships include Nike and Gatorade. After headlining the Nike’s inclusive and adaptive FlyEase series of shoes, she launched her own series of signature shoes, the Nike Air Deldon. She is also the founder of Deldon Designs, a woodworking business.

Elena’s attentiveness to her philanthropic efforts is what sets her apart. Her sister, Lizzie, was born blind and deaf, while also having cerebral palsy and autism. Additionally, during Elena’s time in college, she discovered she was suffering from Lyme disease and has made an effort throughout her career to find a cure. Her experiences led to Elena founding The Elena Delle Donne Charitable Foundation. The foundation aims to raise funds for and awareness of Lyme Disease research and special needs programs. Through her philanthropic dedication, Elena was named a Special Olympics Global Ambassador in 2014.

Barbara Corcoran

Barbara Corcoran’s credits include straight D’s in high school and college and 20 jobs by the time she turned 23. It was her next job that would make her one of the most successful entrepreneurs in the country: She borrowed $1,000 and quit her job as a waitress to start a tiny real estate company in New York City. Over the next 25 years Barbara would parlay that $1,000 loan into a $5 billion real estate business, building the largest and best-known brand in the business.

Corcoran is the author of the best seller “Shark Tales: How I Turned $1,000 into a Billion Dollar Business!” and host of top podcasts “Business Unusual with Barbara Corcoran”.

Corcoran is a motivational and inspirational speaker. She is a frequent small business and real estate contributor on every major network. Corcoran has been an investor/Shark for the past twelve seasons on ABC’s four-time Emmy award winning show, Shark Tank, investing in over 80 businesses to date. Follow Barbara on Twitter and Instagram @BarbaraCorcoran.


Seattle based Multi-platinum and GRAMMY award winning rapper Macklemore made history as an independent artist with a combination of commercial success, critical acclaim and international appeal. Collectively Macklemore’s music videos have been viewed over 3 billion times and he is one of only two rappers in history to have a Diamond-certified single (“Thrift Shop”). His newly released song, the single “Chant” premiered on July 22nd.

Macklemore, an avid golfer, is the Founder of Bogey Boys, a new golf and lifestyle brand. He has a 11 handicap and plays three rounds of golf per week. He plays both recreationally and competitively. He won the 2021 AT&T Pebble Beach Celebrity Shoot Out.

Damian Lillard

Damian Lillard of the Portland Trail Blazers is a 7-time NBA All-Star & a member of the NBA’s 75th Anniversary team. Lillard won a gold medal with Team USA Basketball at the 2020 Tokyo Olympics, and is widely regarded as one of the premier players in the NBA.

Damian is a Co-Founder of Move Insoles, a new athletic health and wellness brand which makes performance insoles for athletes and consumers looking to improve their foot health. Move Insoles was founded in 2020, and has quickly gained momentum as the top insoles product worn among NBA and top college basketball players.

In the offseason, Lillard also known as DAME D.O.L.L.A. is an emerging hip-hop musical artist, who has released 4 studio albums to date under his Front Page Music label.

Marcus Collins

Dr. Marcus Collins is an award-winning marketer and cultural translator with one foot in the world of practice—formerly serving as the Head of Strategy at Wieden+Kennedy, New York—and one foot in the world of academia—as a marketing professor at the Ross School of Business, University of Michigan.

His deep understanding of brand strategy and consumer behavior has helped him bridge the academic-practitioner gap for blue-chip brands and startups alike. He is a recipient of Advertising Age's 40 Under 40 award and Crain's Business' 40 Under 40 award, and an inductee into the American Advertising Federation’s Advertising Hall of Achievement. Most recently, he was recognized by Thinkers50 with the Radar Distinguished Achievement Award for the idea most likely to shape the future of business management. He has also served as a jury for the Cannes Lion International Festival of Creativity.

Before joining Wieden+Kennedy, he served as the Chief Consumer Connections Officer at Doner Advertising and led Social Engagement at Steve Stoute’s advertising agency, Translation. Over the course of his career, Marcus has developed a practice for creating culturally contagious ideas that inspire people to take action. His strategies and creative contributions have led to the launch and success of Google’s “Real Tone” technology, the “Made In America” music festival, the Brooklyn Nets, and State Farm’s “Cliff Paul” campaign – among others.

Prior to his advertising tenure, Marcus began his career in music and tech with a startup he co-founded before working on iTunes + Nike sport music initiatives at Apple and running digital strategy for Beyoncé.

Marcus’ work centers squarely on the impact of culture and the power that comes from having great cultural proximity. His best-selling book, For The Culture: The Power Behind What We Buy, What We Do, and Who We Want to Be, examines the influence of culture on consumption and unpacks how everyone from marketers to activists can leverage culture to get people to take action. Throughout the book, he relies on literature, case studies, his work with brands, and academic data to illustrate the “whys” and the “hows” so that readers will be empowered to successfully apply these learnings in their own pursuits.

Marcus holds a doctorate in marketing from Temple University where he studied cultural contagion and meaning-making. He received an MBA with an emphasis on strategic brand marketing from the University of Michigan, where he also earned his undergraduate degree in Material Science Engineering. He is a Forbes columnist and a trusted voice among CMOs and business leaders. But most importantly, he is a proud Detroit native, a devoted husband, and a loving father to Georgia and Ivy.

Isabella Casillas Guzman

Isabella Casillas Guzman serves as the 27th Administrator of the U.S. Small Business Administration (SBA) and was sworn in on Wednesday, March 17, 2021. Administrator Guzman represents the more than 30 million U.S. small businesses and is committed to helping small business owners and entrepreneurs start, grow and be resilient.
A lifelong proponent of small businesses, Guzman grew up as the daughter of a small business owner and learned at a young age how important small businesses are to the communities they serve, the people they employ, and the economies they help power.

Administrator Guzman previously served as Director of the California Office of the Small Business Advocate, a position she held after being appointed by Governor Gavin Newsom in April 2019. In that role, she served as the voice of small businesses and innovative startups in the 5th largest economy in the world. She administered and advocated for programs and initiatives to help small businesses access capital, markets, and networks for stronger outcomes. She and her team helped connect entrepreneurs in every community with the resources needed. As the economic recovery support function coordinator for the state, she focused on resilience and most recently worked to help small businesses access relief during the COVID-19 pandemic.

In California, Administrator Guzman oversaw a network of small business centers focused on expanding assistance to underserved business groups. She launched new public private partnerships and collaborated to deliver cutting edge resources to small businesses, including through initiatives like Get Digital CA to increase technology and e-commerce adoption and Source Diverse Source Local to strengthen supply chain readiness. She advocated fiercely for financial relief for small businesses, leading to the expansion of state supported lending and the largest COVID-19 grant relief program in the nation at over $2.5 billion. Guzman's office launched the Entrepreneurship Task Force to serve as a bridge to small businesses and create content and programs to help strengthen the competitiveness of startup and small firms.

Administrator Guzman has previously served in leadership at the SBA as the agency’s Deputy Chief of Staff and Senior Advisor during the Obama-Biden Administration, where she oversaw policy and new program implementation. She was a small business entrepreneur herself, and an advisor to fellow founders including in accelerating technology commercialization and in helping small business contractors leverage the federal marketplace. Administrator Guzman earned a Bachelor of Science from the University of Pennsylvania Wharton School of Business.

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