Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Jonathan Beskin, Founder and CEO of SinglesSwag, located in Boca Raton, FL, USA.

What's your business, and who are your customers?

I have two businesses - SinglesSwag and Paradise Delivered.

SinglesSwag is the first and largest monthly subscription service designed for single women. SinglesSwag was ranked #181 in 2020 on the prestigious Inc. 5000 list of the fastest-growing companies in America and #1829 in 2021. The boxes feature full-sized, hand-selected items from categories like organic beauty, skincare, jewelry, fashion accessories, books, delicious treats, and more. Paradise Delivered provides a spa-like, vacation-inspired experience to enjoy from the comfort of your home.

Tell us about yourself

I started SinglesSwag with an idea and a dream when I had no money and a full-time job in finance that I hated. Since founding the company in 2016, the company has generated over $60 million in revenue - profitably - without ever raising a penny in venture capital. I acquired Paradise Delivered in early 2020 and scaled the business from shipping 20 boxes/quarter at the time of acquisition to shipping over 10,000 boxes a month within a year. I am proud to be self-made and motivated by all the haters and doubters that told me I would never achieve anything in my life.

What's your biggest accomplishment as a business owner?

Being in the Top 200 of the Inc. 5000 - it is incredibly challenging to make this list, period, but you are in a rare company in the Top 200. I'm also proud to have changed my life in such a short period and the course of my family's life for multiple generations.

What's one of the hardest things that come with being a business owner?

Owning a business can be a rollercoaster ride with many highs and lows. For example, we did incredibly well with rocketship-type growth from 2016-2020, peaking during the COVID lockdown. This was based on strong and consistent advertising performance, particularly on Facebook and Instagram. In mid-2021, performance on these channels, which had historically performed so well, stopped performing at the same level, primarily due to the Apple iOS privacy update. We needed to shift course in a number of operational areas quickly.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Trust yourself and your instincts. Do not listen to outside voices, particularly those without any real knowledge or background in what you're trying to do.
  2. Be willing to make sacrifices. Scaling a business and changing your life is not easy. Be willing to turn the TV off for better focus, skip a night out with friends, or date night to achieve your dreams.
  3. You can do more yourself than you think. I scaled advertising on Facebook from $10/day to $10,000/day consistently for four years on my own with no prior experience. It was tedious, but I taught myself the platform and learned as much as I could.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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