EP 14: Rob Cummings, Use Storytelling to Pitch Your Start-Up

by | Jan 13, 2020 | Episodes

Rob Cummings is the Managing Director & CTO at Falfurrias Capital Partners, a Charlotte-based, private equity firm that acquires or invests in middle-market businesses. At Falfurrias, he provides management oversight and guidance to their portfolio companies, and leads strategic initiatives for the businesses. He’s also the co-founder of DealCloud — a deal management SaaS platform that’s now in use at close to 1,000 firms participating in lending — and on the buy-side and sell-side of deals. Rob architected the 

original DealCloud software platform. He was also instrumental in growing the business into a major Software-as-Service provider to the mergers & acquisitions industry.  In August 2018, Rob and his business partners sold DealCloud to strategic acquirer, Intapp. Following the acquisition, Rob exited the business entirely but continues to mentor the Charlotte office.

In this episode, we discuss:

  • Why DealCloud used to get “dinged” when they went out to fundraise
  • How DealCloud dominated their “TAM” (their “Total Addressable Market”)
  • How he and Ben (his DealCloud Co-Founder) built the business by giving out their cell phone numbers to clients
  • Why they brought different skills to the business
  • Why software-as-a-service is such a great business model
  • How they built the business sitting shoulder-to-shoulder, with 8 employees in a tiny office at Packard Place
  • How start-ups begin the process of finding investors
  • Why their lead investor was also the easiest person to pitch
  • The difference between working with individual, angel fund, and institutional investors
  • How the DealCloud team successfully managed a “major outage” in 2014, and…
  • Why 95% of their customers were okay with it
  • Why the “free-mium” model in B2B “can be the kiss of death”
  • His “must haves and deal breakers” when he’s watching a pitch
  • His favorite slide in an investor pitch
  • Why you should exit for 10X what you raise
  • What he’s looking for (as in investor) in the Founders of a start-up
  • On how DealCloud created a “deal management system” in the CRM space — “The 10,000 pound gorilla in the space is Salesforce… it’s built for selling widgets, not for doing mergers and acquisitions transactions.”
  • “So the whole model in software-as-a-service is: first you have to land the customer, and it’s all about keeping the customer… You can’t let churn happen. You gotta keep building the business.”
  • “We went out and fundraised in 2012 and weren’t very successful. So that’s one of our failures.”
  • On how to find your lead investor: “Find someone who understand the pain point, inside and out that you’re solving for.”
  • “Failure is a thing and I think everybody goes through it personally and professionally. It’s just something you have to live with and learn from. I think that’s the key.”
Pitch Advice:
  • “Something in a pitch has to grab your audience…  Storytelling with a pitch is the best thing to do.”
  • “To pay someone to spend 8… 14 hours developing the look and feel of your pitch deck is money well spent.”
  • “Think of your [pitch]  slides as back up material to the story you’re telling.”
  • “Have your website match your pitch deck…If your message is different on your website than on your pitch deck… that’s a problem.”
  • “When you’re pitching, if you can, convey your passion. That this is you life. That you go to bed thinking about your company.”
  • “If you can convert your passion, if you can relax, and if you can storytell – I think it goes a long way.”

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