4 Expert Definitions of ‘The Perfect Pitch’

Meet the judges of our $50,000 Dreampitch competition — and find out what they’ll be looking for on June 29

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As we rapidly approach Dreampitch, our $50k pitch competition at TrailheaDX, we’ve been exploring one key question: what makes the perfect pitch? After all, this is an important question to consider not only for the three finalists who will be taking the stage on June 29, but for many of the developers at this year’s conference who are hoping to secure funding and/or sell others on their vision for the future of their product.

And who better to ask this question to than the four rockstar judges who will be crowning the winner of this year’s event? All four of this year’s judges are well-known faces in the world of venture capital, with impressive portfolios under their belts and invaluable experience to share with finalists and audience members alike. Learn more about their stories below — and find out what they’ll be looking for on the big day.

Meet Aileen Lee

Aileen Lee is a seed investor and Founder and Managing Partner at Cowboy Ventures, a seed-stage focused fund responsible for backing many notable early-stage companies — including August, Dollar Shave Club, and Tally Technologies. Previously, she joined Kleiner Perkins Caufield & Byers in 1999, and was founding CEO of digital media company RMG Networks, backed by KPCB. She also coined the often-used Silicon Valley term ‘unicorn’ in a 2013 TechCrunch article, “Welcome To The Unicorn Club: Learning from Billion-Dollar Startup.”

Aileen Lee, Cowboy Ventures

“I look for founders with a relevant personal connection and unique capabilities for the mission their company is on, as well as unique technology and insight into a large potential addressable market. I want to hear about the company’s mission, what’s been figured out so far, and the goals for the next 1–2 years — explained in a linear way, and with excitement.”

Meet Scott Raney

Scott Raney is a venture capitalist at Redpoint Ventures, a venture firm based in Menlo Park, CA with approximately $2B under management. Scott serves on the boards of Guild Education, Sourcegraph and Twilio; he also led Redpoint’s investments in Expensify, Hashicorp, Platform9 and Stripe. His past investments include adap.tv (AOL), Cloud.com (Citrix), Heroku (Salesforce), Jumptap (Millenial Media), and RelateIQ (Salesforce). Prior to joining Redpoint, Scott was responsible for new products at NorthPoint Communications, a data CLEC providing nationwide DSL services, and ran engineering for VideoPort Technologies, a startup developing videoconferencing solutions.

Scott Raney, Redpoint Ventures

“A great pitch tells a story about the problem you are trying to solve, how you will solve it and why you are the right team to do it. But, most importantly, it should convey the passion the entrepreneurs have for their idea.”

Meet Arlan Hamilton

Arlan Hamilton is Founder and Managing Partner of Backstage Capital, a venture capital fund on a mission to minimize funding disparities in tech by investing in high-potential, underrepresented founders — including women, people of color and the LGBT community. Having previously founded and published the internationally distributed indie magazine INTERLUDE (and continuing to serve as tour manager to Atlantic Records recording artist Janine), Arlan entered the venture investing world from an unconventional path. Backstage Capital has now invested nearly $2M in over 40 companies.

Arlan Hamilton, Backstage Capital

“What I hope to see in a pitch is confidence in your product, your market, and yourself, coupled with the humility to know that none of us have all of the answers. I’m drawn into pitches that have an authentic quality to them, and are delivered in a way that shows the founder lives and breathes their company. It’s also prudent to highlight your traction without sugarcoating or embellishing, since most investors can see through smoke and mirrors relatively easily.”

Meet Josh Stein

Josh Stein is a partner at DFJ, where his current board responsibilities include Box, Chartbeat, SugarCRM, and Talkdesk — to name a few. His previous investments include Eventful (CBS Local), GoodGuide (UL), iList (IGN/News Corp), Selligy (Veeva Systems), Swell (Apple), Yammer (Microsoft), and Twilio. Prior to joining DFJ, Josh held leadership positions at Telephia and ViaFone, a DFJ portfolio company, as well as product management positions at Microsoft and NetObjects. In 2013, 2014, and 2015, Forbes ranked Josh in their annual Midas List of top technology investors; in 2015, he was named by Deloitte as the Venture Capitalist of the Year. The New York Times / CB Insights have also recognized Josh as a top VC investor in 2016 and 2017.

Josh Stein, DFJ

“We’re looking for entrepreneurs who are ‘thinking big’ and who have bold plans to go after large market opportunities. Big ideas, especially when tied to a broader sense of mission and purpose, have the power to inspire both financial capital and human talent, the two key ingredients for building a business. When considering an investment, our first question is ‘how big would this be if it works.’”

Don’t miss Dreampitch on June 29th!

Headed to TrailheaDX? Be sure to catch Dreampitch at 11:30am in the keynote room to find out who will take home one giant check — and see our four rockstar judges in action.

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