The Unfinished Product

The Reality of Becoming The 'New' CEO with Anna Tsyupko

Anna Tsyupko Season 1 Episode 1

In this episode I'm joined by Anna Tsyupko, Founder @ Expansion Zone.  Anna’s startup journey epitomizes the idea of  being thrown in at the deep end. After just a few years working at a family office, Anna was brought into a portfolio company as their CEO to turn things around. Following that, Anna moved on to become COO at another high-growth fintech and has now started a new coaching venture.

Trailer (The high level journey): Investor @ Family Office > CEO @ Paybase (Acquired) > COO Tomato pay > Founder @ Expansion Zone

Outtakes (the moments few people saw, but shaped everything): 

  • The feeling of walking into an organisation of 20 as the new CEO
  • Pivoting and growing a company towards an exit 
  • Actually listening to customers and building products that scale  
  • Understanding what you love about your role and focusing on those elements in future roles 
  • Knowing when you’re nearing burnout and doing something about it 


Edits (the things you might have done differently, if you could go back)

  • Listen to find out!