Startup Pitch Decks

A few weeks ago, Alex Iskold of TechStars NYC asked me to talk with the Winter 2017 class about constructing an effective fundraising pitch deck. I jumped at the chance because this is an important topic that often comes up with first time and even repeat entrepreneurs when they’re about to embark on a fundraising process. In my short career as a VC, I’ve reviewed thousands of pitch decks and helped hundreds of founders refine their pitches. Additionally, I’m often approached by founder friends to provide feedback on their slides before they go to market. Given pitch decks are frequently discussed and they’re essential in the fundraising process, I thought it would be useful to create a simple guide to building an effective pitch deck.

Our goal with ‘Startup Pitch Decks’ is simple: to provide founders with a simple framework and reference guide that can be utilized before kicking off a fundraising process or when you’re in the throes of drafting your pitch deck. We dive into a number of topics including the ideal format, a sample build process, tips and tricks, advice from RRE founders, and even things to avoid. We’ve tried to make the guide as comprehensive as possible but realize it’s impossible to include every piece of advice and address every question. As such, we’d love to hear your questions, suggestions and feedback. Our aim is to evolve ‘Startup Pitch Decks’ with your help and input so it gets more useful over time.

All that said, it’s my pleasure to present Startup Pitch Decks. Hope you find it useful, thought provoking and perhaps even inspiring.

(Finally, I’d like to thank my colleagues at RRE — Jason Black, Alice Lloyd George and Cooper Zelnick — for providing feedback and adding some polish to the final product)

Why I Invest

Last Friday night after a long week, I decided to go for a long run and listen to a Buddhist lecture on the true nature of existence and the self. About ten minutes into the run, I started to contemplate why I have chosen various paths in life such as becoming a venture investor. Since I have decided to make this my life’s work, I began to examine what really drove this long-term decision and whether I was being honest with myself. As soon as I returned home and showered, I opened up my computer and published the following tweet.

Ryan Hoover of Product Hunt was the first to reply and suggested that I expand on the tweet and provide commentary and context on each one. I hadn’t considered writing a post, but ultimately decided it would be enlightening and cathartic to dive into each reason and expose myself.

Below is an expanded view into all the reasons that I have chosen VC as a career. I’ve also tried to be honest about what drives me. While this list captures how I feel today, I’m sure it will evolve over time as I learn more about myself and my worldview changes.

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Here’s How My Wife Helped Me Become A Better VC

I am a VC. My wife is a founder. When I walk into our apartment at the end of each day, my role morphs from investor to husband but I also become a motivational coach, sounding board and sometimes even a punching bag. There’s virtually no barrier separating my life from entrepreneurship. It’s a constant. I have a completely unfiltered view into the life of an entrepreneur. I see the wins, the losses and everything in between. This situation has helped me gain a deeper appreciation for entrepreneurs and the daily battles they endure and sacrifices they make.

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A Bunch Of VCs Went On A Retreat. Here’s What Happened.

This past weekend I had the good fortune of participating in the first Reboot VC Bootcamp. For those of you who don’t know Reboot, it’s a values-driven organization led by Jerry Colonna that primarily helps founders and their teams deal with the constant ups and downs of startup life. At the most fundamental level, Reboot is a personal development company that offers bootcamps, executive coaching, 360 reviews and a variety of other programs to help leaders discover their true selves. Reboot also publishes useful and powerful content including a phenomenal podcast hosted by Jerry. I can’t say enough great things about this organization, its team, and their mission.

This formula is the essence of Reboot:

PRACTICAL SKILLS + RADICAL SELF-INQUIRY + SHARED EXPERIENCES

= ENHANCED LEADERSHIP + GREATER RESILIENCY

Jerry and Brad Feld, a Partner at Foundry Group and Co-founder of Techstars, decided to run a bit of an experiment. Instead of facilitating a boot camp for founders, they tailored a program designed specifically for venture investors. Jerry and Brad have over forty years of combined investment experience. They’ve seen the good, the bad and the ugly. Most importantly, they deeply care about the startup ecosystem and believe in paying it forward. When they’re in a room together the discussion is always authentic, insightful and inspirational.

Over the weekend, sixteen investors from funds of all sizes and both coasts descended on Boulder, CO to speak openly about our challenges and to learn how to improve our interactions with our portfolio companies and the founders we work with. Jerry and Brad worked closely with the group to help us uncover our authentic leadership styles and provided practical skills for managing the array of feelings that can be triggered as we navigate the startup ecosystem. The goal of the weekend was to help each of us become the best board member, investor, supporter that we can possibly be.

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Investing With A New Purpose

Several weeks ago, I was hanging out with Lindsay Ullman of Sidewalk Labsand we were talking about some of the companies I’ve backed at RRE andLerer Hippeau Ventures. She paused at one of them and asked, “Do you believe this company is good for the world?” Candidly, I was caught off guard. I wasn’t expecting such a direct question and didn’t consider it much when I was making the initial investment. I didn’t know what to say.

Over the last few weeks, I’ve thought about my conversation with Lindsay at least a dozen times. Her question forced me to be honest with myself about the reasons why I funded this startup, and the rationale behind some of my other investments too. I realized that my investment philosophy had been slowly changing for some time, and our conversation was a kind of tipping point. I finally arrived at the following conclusion: If a company doesn’t solve a worthy problem and make the world a better place, then I have no business investing in it.

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Don’t Congratulate Me For Writing A Check

On Thursday we announced our Series A investment in Managed by Q. Throughout the day, I received countless congratulatory emails and tweets from friends. “Amazing investment.” “Love that company.” “Nice win.” “HUGE CONGRATS.” And so on. On my way home, as I reflected on these kind messages, it occurred to me that I don’t deserve a pat on the back. There’s a long road ahead for the company, and I really haven’t done shit. Sure, I built a relationship with Dan and Saman, hustled to help Q win new customers and key employees, and gave them a generous term sheet. But writing a check is easy. Being an engaged board member and a supportive partner in good times and bad is the hard part. And building an enduring, category-defining company is nearly impossible.

Mark Cuban once said, “the magic in business isn’t raising money but making money.”

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Improving Human Interaction

While on vacation I decided to finally read the timeless classic by Dale Carnegie, ‘How to Win Friends and Influence People.’ The book was first published in 1936 and has sold more than fifteen million copies worldwide. It’s the granddaddy of all people skill books. Many of the lessons contained within are still relevant for anyone that deals with people.  Given Venture Capital is a highly social business with thousands of human touch points each year, this book was probably one of the most important I have ever read. 

We have a saying at RRE that our brand is the sum total of the positive and negative interactions that someone has with our team. Every touchpoint matters regardless of the medium (face to face, email, social media, etc.) and those involved (founders, limited partners, other VCs, etc.). At the most fundamental level, we operate in relationship-driven industry so we’re only as good as the interactions that people have with us (and of course the success of our investments). 

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Update My VC

Today we are launching Update My VC - a modern guide on how founders can easily update and keep in touch with your investors. At RRE we always strive to provide the best possible support to our companies, but we realize you’re slammed building product, growing your business and recruiting the best talent. We also understand the last thing you want to think about and have time for is sending a lengthly update to your investors. 

To make this process easier for you, we’ve created a Tumblr blog that outlines the perfect investor update. Our template includes Highlights, Lowlights, Product, KPIs/Core Metrics, Business Development, Hiring, Financing, Press, Help Wanted, and Kudos. The site even has an Email Template button that auto generates a blank investor update as a new email message.

Additionally, we’ve included a library of resources including useful blog posts, slideshares, and Quora discussions.  Our expectation is to update this library so the most useful content and advice is all in one place.  We view this as an evolving site and community so feel free to share your questions, comments and feedback with community@rre.com

Finally, I’d like to thank Amrit Richmond and Kane Hsieh from the RRE team for their help in launching this site. 

Why Saying No Is Hard

Being an investor isn’t easy for a number of reasons. But the hardest part for me is saying “No.” I meet hundreds of entrepreneurs each year, and at RRE Ventures we invest in only a small percentage of them. VC’s generally invest in less than 1% of companies they meet. So if you do the math, you know I have to say “No” a lot.

There are countless reasons why we choose not to back an early stage venture. Market size. Wrong team. Bad timing. Competition. Traction. Lack of monetization. Little or no competitive advantage. Outside our expertise. Valuation. I could go on. 

But regardless of whether I exchange a quick email with a founder or spend hours getting to know him or her, passing is the worst. It’s the only part of my job that I truly hate. And it’s not just because I lose the option to invest down the road. I hate passing because my daily work with entrepreneurs has given me a good look into their struggles…what founders sacrifice daily to ensure that their company is in a better place tomorrow than it is today. It becomes personal, emotional…it's only human to feel for the founders who…

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Nail Your Seed Round

Several years ago I started teaching a class on raising seed capital at General Assembly and Skillshare.   I initially created the class because friends and founders were coming to me for fundraising advice and I was answering generally the same questions over and over.  

A few months ago, I realized the initial slideshare that I used for dozens of classes was good as long as there was a voiceover but not great as a standalone guide. I decided to speak with a handful of my students and founders to see what they would want in a v2 fundraising resource.  

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Betting The House on NYC and Joining Lerer Ventures

Only a year ago I decided to leave my dream job at The Kraft Group / The New England Patriots to jump head first into the NYC startup scene.  During my time at The Kraft Group, I focused on early stage investments, strategic partnerships and digital media strategy.  While I enjoyed living in my hometown of Boston (Go Sox!) and working for a highly respectable and influential company, I recognized something special was happening a few hundred miles south. The NYC tech community was heating up, and I was itching to join a startup.

That opportunity came when Billy Chasen and Seth Goldstein of Stickybits (now Turntable.fm) made me an offer to join the company as their VP of Biz Dev and first business hire.  I arrived last summer and worked out of DogPatch Labs. Immediately I realized that the startup culture here had a distinct energy and momentum, different than anything I had experienced in Boston, Seattle, Austin, New Orleans or LA.

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