Mike Wilner, Founder & CEO of Upside


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The freelance economy is quickly growing from a marketplace dominated industry to a robust ecosystem with 10 different segments. 

One of the most fascinating segments is the freelancer focused tools and solutions that enable freelancers to scale their businesses without needing a platform, or in tandem with a platform. 

Upside is one of these exciting new startups leading the solopreneur charge. By monetizing referrals, Upside enables freelancers, consultants, solopreneurs, whatever you want to call us, to monetize our network in a way that’s a win-win for us, our clients, and Upside. 

In this episode, we’ll open up the hood to why Mike is building Upside, how he got to the insights of starting Upside (hint…he has been in the space for a while), and where he sees the freelance economy going.  

You will also meet an incredible founder, Mike Wilner. Before Upside, Mike built a freelance web design marketplace in 2015, Co-Authored the book Oversubscribed, and worked at Amazon Web Services.

Key Takeaways:

  • Traditional marketplaces face challenges in retaining top talent and generating demand.
  • Upside is a partnership platform that empowers individuals and small firms in the professional services industry.
  • Successful referrals are the core metric for Upside, enabling users to share opportunities and collaborate.
  • The future of the freelance economy lies in uncapping the potential of individuals and creating infrastructure for collaboration and business development.


00:00 – Introduction and Background

04:23 – Challenges of Traditional Marketplaces

18:21 – Upside: A Partnership Platform for Professional Services

34:17 – Customer Profiles and Referral Behavior

40:47 – The Future of the Industry

Follow Up Material & Links

This episode is brought to you by We Are Rosie. We Are Rosie is a trusted partner to over 200 companies, from high-growth startups to global brands you know and love. 

Powered By Human Cloud, the global authority on the freelance economy. 

Human Cloud helps freelance leaders solve their toughest challenges. From Enterprises scaling freelance workforces, to Platforms positioning their unique differentiation, Human Cloud is fortunate to have a global hand in helping the freelance economy grow.


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