March
24, 2021
12 min read
In this ongoing series, we are sharing advice, tips and insights from real entrepreneurs who are out there doing business battle on a daily basis. (Answers have been edited and condensed for clarity.)
Who are you and what’s your business?
Andrew Reiner, co-founder of Grapevine AI. My infatuation with entrepreneurship started when I was 15 — building a company that I grew to over 250 clients and sold before even enrolling in college. After graduating from Babson College, I worked at Lehman Brothers and Barclays Capital in capital markets. Then I evolved into a quant jock at Zweig-Dimenna Hedge fund and in 2012 left to become the COO for SeatServe, an in-seat delivery platform for stadiums, venues, and ran all things sales, hiring, GTM, and was the fundraising “ninja,” raising two rounds of capital. Because paying it forward has always been a big part of who I am, I advise several startups and mentored for Halcyon Accelerator.
What is Grapevine AI?
We’re building the first voice-driven, real-language relationships insights platform. Essentially, we let you just ramble about who you met, what’s important to them, and what you need to do next and we take care of the rest. It’s as easy as having a conversation with yourself. Just click a button and start capturing intel on your contacts: Bob loves the Mets, Jane’s quota is due at the end of April, or Elizabeth has two kids named Peter and Lucy. Whatever is important to you is important to us. But even better, we can recall this information, just by asking real questions about anecdotal details. Grapevine AI will help you genuinely connect with your prospects or associates because we won’t let you forget the details that may mean the world to your contacts. Think of it as your personal handler!
What inspired you to create Grapevine.ai?
I was at a wedding up in Cape Cod and I saw a 65-year-old guy wearing a Knicks hat. I immediately thought 2 things: 1) I’ve never seen someone wear a baseball hat to a wedding and 2) I’ve never seen someone with the stones to wear a Knicks hat this close to Boston. I love meeting new people, so I decided to go talk to him. Over the next 30 to 45 minutes we talked, we laughed, and I learned a bunch of things about him. He’s a doctor from the Upper West Side of Manhattan, he’s drinking Macallan 12, he’s obviously a Knicks fan, and I thought to myself: I need to introduce him to my dad. They’re about the same age, doctors, both of them love the Knicks and a good glass of whiskey, but most importantly they’re both horrendous but entertaining dancers. The problem came the next morning when I forgot his name! It really pissed me off that I couldn’t remember one person’s name from the night before and it made me pause — what else am I forgetting? How am I supposed to build relationships with people over six months, 2 years, the rest of my life? There needed to be a better way to focus on building the actual connection and there needed to be a way to use artificial intelligence and voice technology to do so. This is why we developed Grapevine AI.
Related: How This 18-Year-Old High School Student Built a 6-Figure Social Media Consulting Business
We created Grapevine AI because scribbled notes on cocktail napkins, Post-Its or whatever cockamamie system you use just isn’t cutting it anymore. Why not whip out your phone and quickly talk to Grapevine? You’ll never scramble before a sales call or meeting because reminders about key details (personal and professional) will be curated and delivered to you in Grapevine AI’s Daily Intelligence Briefings.
What has been your biggest challenge during the pandemic, and how did you pivot to overcome it?
Team-building, fundraising, and figuring out how we can adjust our product to the new normal of back-to-back Zoom calls. So much of what I value in leading a team is building a strong, cohesive group of individuals who can work hard and play hard — together! Of course, with Covid, gone went Friday beers and Playstation tournaments. So we started Thursday zoom game days–everything from Mario Kart to trivia games–to keep us all connected on the fun front. It was necessary, critical even, to communicate with each other. We offered $10/day to our employees for lunch and a blank check for everyone to order a lovely meal (for them and their spouse) for the holidays so that we could have our “holiday zoom” together as well.
Related: This Entrepreneur Is Building a Platform to Inspire the Next Elon Musk
From the fundraising perspective, I’m much better in person because half of what I try to do is read body language, which is obviously more complicated to do over Zoom. The flip-side to this is we were able to meet with notable investors from all over the world and now have a global network of amazing investors. People are more receptive now more than ever to meet with folks from outside their network/region. We were really fortunate to have a fantastic team and a great product that fundraising over zoom was manageable -– we found people really resonated with the problem we are trying to solve, and it didn’t matter that our pitch wasn’t in person.
From the product side, it was vital for us to evolve our platform to use it both on the go and at your desk. It’s why we created a web-based dashboard that utilizes our cutting-edge AI and have plans to integrate into Zoom this year.
What advice would you give entrepreneurs looking for funding?
First, let me just highlight the different investor channels you should be aware of:
-
Friends and family → easiest capital to attain if you have the network, hardest money to ask for. If you are unwilling to ask those closest to you, you send a “lack of conviction” signal to investors.
-
LinkedIn → cold outreach here isn’t the worst idea.
-
Angel.co → get a feel of what type of investor invests in your space.
-
Crunchbase → get a feel for what your competitors have raised and from whom.
-
Signal.nfx.com → see active investors in your space; find common acquaintances to ask for introductions.
-
Syndicate Groups → Typically invest in later stage “down the pipe” investments, but a great way to add strategic LPs to your cap table.
-
Venture funds → Depending on your stage, traction, this could be an excellent signal for your startup. It also generally comes with other strings attached (read: board seats, pro-rata rights, etc.).
-
High signal investors → who is the best investor for you? Who can help you go from 0→ 1 or 2→ 4 through their own network or experience?
Next, let’s talk about how to approach investors and who to approach first.
In my opinion, start with friends and family. Take small checks. Give them good terms. Reward them for supporting you early. Then move on to angel investors and venture funds if you decide that’s the correct route. These are generally more challenging to be introduced to & it’s usually one of the founder’s jobs to find a mutual/warm connection to an investor. The best thing is that if you leave a good impression with one investor, they are usually willing to make an introduction even if they pass on the round. Whenever someone passed on us, I always asked for value-add introductions. This creates a spider web of connections creating a network effect almost immediately.
The best way to ask for an introduction is to establish credibility with whomever you’re talking to and send them an email they can forward. I use a similar template that Alex Iskold (of TechStars & 2048.vc) popularized that you can find here.
It’s essential to identify who you think adds value to your cap table and who can help you grow quickly. I believe that there are three ways for investors to add value. One is for you to scale through their portfolio companies, which is an obvious value-add. The second way is to be a brand ambassador to help you go viral. The last way is to increase your knowledge through conversation and whiteboarding–helping you identify future channels for fundraising and general advising. It’s even better if they can help shop your venture to other investors. I would rather have a cap table that crunched my valuation filled with strategic investors than a lofty valuation from people who add no value. Most cap tables I know of have a blend of both types of investors.
Related: The First Female RV Company CEO on Bringing Ultra Luxury to Land Travel
I’ve used signal.nfx.com a few times for finding direct connections to investors through my network, but I don’t believe I’ve ever received a check from this route. Most syndicate groups passed on us because we were pre-revenue and pre-launch, but one of the world’s largest groups believed in our vision and came in with a substantial check. Syndicates, in my opinion, are great, you get loads of LPs who are brand ambassadors and potential pilots or revenue channels, but you only deal with one manager and one entry on your cap table.
How best to prepare for a pitch meeting?
I like to think of preparing for a pitch as 60% know your shit, 30% show your passion, and 10% understand who your audience is. Never ever read a pitch. It’s obvious. You might think it’s not because you’ve enlarged your font so your eyes don’t move or some other trick, but it’s almost impossible to fake enthusiasm and passion while reading a teleprompter.
The key is to know your stuff. Know the big talking points per slide—practice, practice, practice. Record yourself. Listen to yourself — even if you find it cringe-worthy (I know I do). Identify how you can improve. Practice some more. Research your industry, know your competitors. Know your key differentiator, where the market is and how it’s yours for the taking. Then practice some more.
Then, when you’re ready to pitch folks, pitch people who you think are least likely to invest in your startup. Whether you’re too early for them, or you don’t fit their actual thesis, or if you doubt they have the cash to invest. Practice pitching on them. They will ask you questions you are unprepared for, but it’s ok because the odds of you closing them are small to begin with. After you get more comfortable answering the same questions most people will ask, move on to folks you think there’s a slight chance of closing and pitch some more. They will ask different questions. You will start to become better at answering them on the fly. Then, finally, go after those that you think you have the best shot at closing. By now, you have pitched a few dozen times (hopefully) and have worked the kinks out of your system. You will seem SO much more prepared during the Q&A section of the pitch because you’ve already heard and responded to most of the questions they will ask. You will shine. The investor will think you are a rockstar – and you are a rockstar – but not because you just know everything. You’re a rockstar because you saved the best for last, and now you are so much more prepared than you were when you pitched the first investor a few weeks prior.
What does the word “entrepreneur” mean to you?
An entrepreneur is someone who is always trying to find a better way to solve old problems. Someone who gets told no, and instead of being dejected, tries to learn why they heard no. Someone who’s willing to risk it all – betting on themselves and their ability to execute. Someone who can’t have a boss and wants to change the world, one small segment at a time. An entrepreneur craves the rush and loves feeling like they beat the system. Ultimately, it’s someone who loves winning and always thinks, “I can do it better.”
Is there a particular quote or saying that you use as personal motivation?
When I was younger, like 12, my dad and I used to long-distance run together. He was a consistent marathoner. Whenever I was tired or needed a break, my dad would look at me and make me scream, in Central Park or wherever we were, “I’m a fucking animal!” and keep going. Single-handedly the most motivating thing anyone has ever said to me.