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Starting a business from scratch is an adventure.

In the episodes below we dig deep into the systems, secrets, and stories of remarkable people who dropped everything to start a healthy profitable business.

Dec 17, 2017

So you’ve got a million dollars that your looking to invest right?  It’s just sitting around in your side table or stuffed into the cushions on your couch but you know it should be invested somewhere so it can grow into two or three million.  You could invest in the stock market or real estate but that sounds so boring.  You want to invest in ideas, great ideas, and help them grow into a multi-billion dollar company like Amazon or Google. 

If that’s your scenario, our guest today is the right guy to call.  Serial entrepreneur Mike Trotsky has started tech businesses, sold them, and connected hundreds of investors with opportunities to fund great tech ideas.  In our conversation, he breaks down the western frontier of investing into terms we can all understand.


Here’s an overview:

  • How it all Started

Mike went to college at Indiana University to be an audio engineer.  He and some friends started building online donation systems for political campaigns.  That business, called Worldview, grew and they became the tech behind a bunch of political campaigns in the late 1990’s.


Eventually they moved away from the consulting congressional campaigns and tried to go deeper into the dot com boom.  They couldn’t scale with consulting so they shifted to a tech solution to making rent payments.  This was the first tech solution they came up with that took on investors and was really scalable. 


  • What is Sproutbox?

As the name implies, Sprout Box offers everything a new seed business needs to blossom.  The investors are there, the expertise is there, and the services like lawyers, financial advisors, etc are there.  An entrepreneur who gets in isn’t guaranteed success but he or she couldn’t be set up better for it.  Most of the businesses they launched offered tech oriented SAS products.  That means Software as a Service.  In other words, the software that the business creates provides some kind of service.  That could be connecting a driver with someone who needs a ride (like Lyft or Uber), helping a beekeeper analyze her hives (like BeeCorp), or revolutionize software billing processes like Cheddar the business Mike would engage with beyond Sproutbox eventually becoming the CEO.


  • What is Cheddar?

Cheddar is a business that created a billing system that sits behind a ton of SAS (Software as a Service) products.  It basically functions as the cash register for tech products.  Their product is on the cutting edge of tech billing helping companies to bill based on use (like your water bill).


‘I’ve found this problem’ is way better than ‘I’ve got an Idea’



  • What are the investing steps entrepreneurs go through as there business grows?

Every business goes through a different evolution, but here are the basic stages where entrepreneurs generally ask investors to join:

  • Friends & Family Round ($10K to $50K)– As it sounds you pitch your company idea to the people closest to you and hope to raise small amounts of cash from them. This is a point where you can join an Accelerator as well.  These are basically programs the pay ten to fifty thousand dollars and help you get going.


  • Angel Investors ($50K-$300K) – These are individuals who may not know the entrepreneur personally but are generally connected in some way. They might be in the same town or connected through a local eco-system


  • Seed Stage ($500K-$4M) – Now groups of investors are involved. The business has proved itself and it’s shown an ability to scale


  • Series A, B, C, D – This is the big time. Major Venture Capital Firms (VCs) and making multimillion dollar bets on established businesses.  The entrepreneur has shown scalability and it’s just a matter of marketing the product and scaling.


  • IPO – Going public and being publicly traded on the stock market.






Special thanks to Mike Trotzke for taking the time to share the Sproutbox & Cheddar story with us.  You can find him at:

Cheddar -

Sproutbox –


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