Empowering Entrepreneurs Conquering Challenges with Lessons in Delegation and Growth
How can entrepreneurs develop resilience and confidence to overcome the fear of judgment and criticism?
Jonathan Beskin is the Founder and CEO of SinglesSwag, a subscription service designed to empower single women. In less than five years, Jonathan's startup has accumulated $60 million in revenue. He has been featured twice in the Inc. 5000 list.
Jonathan Beskin began his career in banking but quickly realized that it wasn't his true passion. Despite always wanting to be an entrepreneur, Jonathan struggled with self-doubt and anxiety. His entrepreneurial journey started while he was a business school student at FAU, where he enrolled in an executive program designed for working professionals.
During this program, Jonathan studied real-life case studies of businesses with recurring revenue models, such as Netflix and Birchbox. Inspired by these discussions, he made the decision to focus on starting his own recurring revenue model business instead of solely advancing his career. Jonathan chose to keep his current job and devoted his efforts to building his own business in this field.
Jonathan shares his experiences, challenges, and successes as an entrepreneur, providing valuable insights for aspiring business leaders. Here are three key takeaways from this inspiring episode:
🔑 1. Embracing Anxiety as Fuel: Jonathan discusses how he channels his baseline level of anxiety into his business. By thinking about various aspects, such as competitors, customers, and industry trends, he stays ahead in the game and drives positive change.
🔑 2. The Power of Discipline: Jonathan's marathon running background has taught him the importance of discipline, which he believes is crucial for entrepreneurial success. He shares how sacrifices and a strong work ethic have helped him maintain focus and build a thriving business.
🔑 3. Delegating and Prioritizing: As his business grew, Jonathan realized the need to delegate tasks and prioritize higher-level strategic decisions. He reflects on the challenges of letting go, trusting others, and becoming a better leader.
Empowering Moments
00:21 Serial entrepreneur inspires others to believe in themselves.
05:30 Unhappy in banking, pursued entrepreneurial journey.
10:53 Traumatic experiences, job struggles, but eventual success.
13:19 Business challenges, skepticism, logistical issues, personal struggles.
16:29 Limited access to mentors, seeking own solutions.
21:57 Value in doing it on your own.
24:39 Started small, doing everything; became addicted. Needed to delegate to grow. Trust issues hindered progress. Hired mother to ease workload. Learned to let go, prioritize strategic decisions. Created in-house brands, saved money. Challenging but evolving into better leader.
31:12 Overwhelmed with 20 jobs, needed help.
34:05 Entrepreneur regrets not delegating tasks for growth.
38:58 Anxiety and depression never truly disappear.
40:59 Incredibly disciplined marathon runner turned successful entrepreneur.
46:42 Endgame: Find happiness, be carefree, inspire others.
50:54 Last question made me realize I'm happy. Find me on Instagram, TikTok, and my website. Book coming soon.
52:45 Enjoy life, make strides, keep going.
Running a business doesn’t have to run your life.
Without a business partner who holds you accountable, it’s easy to be so busy ‘doing’ business that you don’t have the right strategy to grow your business.
Stop letting your business run you. At Harper & Co CPA Plus, we know that you want to be empowered to build the lifestyle you envision. In order to do that you need a clear path to follow for success
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Copyright 2025 Glenn Harper
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