Jake was inspired to start Groundbreaker because he experienced the pains of managing fundraising and investor relations using basic office software tools. He underwrote distressed hotels in the 2008/09 downturn and spent more time cleaning up data and documents than doing the actual analysis. Between sending out PowerPoint presentations to investors one by one and booking investments in an Excel sheet, it became clear that this way of handling the business was inefficient.

After spending some time working in the technology sector, Jake connected the dots and realized that everything he was doing could in some way be automated to save thousands of hours of work and improve quality at the same time. Shortly thereafter, Groundbreaker was born as the first solution to automate the fundraising and subscription process for private real estate syndicates.