8 tips for successfully pitching an investor

Our friends at the Young Entrepreneurship Council asked eight entrepreneurs to share their top tips for pitching investors, based on their own success and failures. Here’s what they found:

Share your vision, not a product tour

It’s a rookie error for an entrepreneur to pitch an investor with the equivalent of a product tour. Investors are usually more interested in the big picture — your vision for your business, why they’ll be a good match, and how your company will return their money handsomely. If your slide deck or in-person presentation seems to linger too long on touring your site or demonstrating your product, it may convey that you don’t have a sense of the larger mission.

Spend less time on the nitty-gritty upfront; rather, capture the investor’s interest with your passion for the bigger picture. Once the investor has a sense of that, s/he can always ask you for a deep-dive into the product tour. And if they do, it likely means you’ve piqued their interest.

– Doreen Bloch | CEO / Founder, Poshly Inc.

Find the true believers

Investors will mostly say no. And contrary to what many entrepreneurs may think, it’s not your job to convince them why they’re wrong but, instead, to find investors that think you’re right. I’ve found that’s the hardest part, really — spending time speaking with investors who aren’t convinced can be a huge waste when, but at the end of the day, they aren’t likely to invest in something they’re not sure of to begin with. That’s their job.

Not heeding this has been my biggest mistake so far in fundraising and pitching — and eaten up time I could have been searching for true believers and advocates instead.

– Derek Flanzraich | CEO and Founder, Greatist

Win the battle at the beginning

When pitching to an investor, you’ve got to win the battle ahead of time. I think doing PR and branding work for your company in advance is important. Make sure that when someone Googles you, they see great results. Make sure you’ve built a relationship with one of the partners at the firm. The deal should already be close to being done before you pitch; the “partner meeting” is supposed to be a formality that allows the other partners to feel good about the deal and ask their questions. If you are talking to an individual investor make sure you have milestones that align with your financial projections. Anytime I’ve been able to inform an investor exactly how we plan to produce the projected revenue concisely and clearly, we’ve gotten the deal done.

– Raoul Davis | CEO, Ascendant Group

Know what an investor fears

The biggest thing an investor fears isn’t what you think it is. Investing in something that fails isn’t an investor’s biggest concern. The thing an investor truly fears most is missing out on something big. The surest way to land an investor is to convince her that your project is a big opportunity not to be missed out on. The best proof of your opportunity is social proof, specifically by having other respected investors on board. Once you find one eager investor, the rest are easy.

– Corbett Barr | Founder, Insanely Useful Media

Be cocky to seal the deal

My team and I are super nice people. We originally walked into investor meetings with a huge smile on our faces and a perfectly practiced pitch. Unfortunately, we found out that nice guys finish last. It wasn’t until we changed our approach that we finally closed our million-dollar round.

Instead of being friendly and nice, we acted cocky and brash, as if the investor was lucky to be meeting with us. Of course, we were still very respectful, but we stayed away from thanking them for the meeting or sounding too eager for their money. We successfully closed investor pitches when we mentally decided that we are the prize and that the investor needs to impress us in order to take the money.

– Jun Loayza | President, Ecommerce Rules

Communicate your milestones to build confidence

Potential investors want to know where their money is going and what their investment will help you to accomplish. Perhaps most importantly, they want some assurance that you will wisely use their money to hit milestones that will, in the future, allow you to raise additional money.

Instill your would-be investors with confidence by clearly connecting the dots between their investment and your business goals. Create a compelling narrative that shows that you will be able to accomplish X, Y, and Z with their money — which will most certainly guarantee future investments.

– David Ehrenberg | Chief Financial Officer, Early Growth Financial Services

Do your homework

The golden rule for meeting with investors is doing your homework. There are two things you absolutely need to know: which industries they invest in and what prior investments they’ve made. This is really the bare minimum; it’s also nice to know a bit about their personal and professional background: where they went to school, what they’ve been posting about on their blog, and what outside interests they have.

These things will help target the conversation and demonstrate that you’re a professional and have done your research. You need to show these people that you’re a capable and reliable recipient of their money, and solid preparation will help you jump out of the starting gate in good style.

– John Harthorne | Founder and CEO, MassChallenge

Do not talk valuation

Talking valuation during a pitch is shortsighted for an early-stage investor pitch, and just one of many components that will be discussed at a later stage of the investor discussion. Instead, focus on the team and the technology (you should actually show it to them). Clearly explain the stages of your startup and the reasons why you are requesting a certain dollar figure. Keep the dollar figure on target to a run-rate to achieve your goals through that stage.

– Carmen Benitez | Co-Founder and Managing Director, Fetch Plus

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

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4 Ways to Turn a Floundering Business into a Thriving One

My business nearly tanked in 2012.

When I launched Transcription Outsourcing in 2010, our primary focus was providing transcription services to medical practices and hospitals. My business started out on a strong growth track for the first couple of years, then profits began to trail off. As many businesses in the medical industry moved to voice recognition systems, new leads began to shrivel and our projections sank.

I realized we had to make some serious changes to avoid going under, and began a complete overhaul of the services that we offered. We also diversified our client base, and today only half of our business is in the medical industry. The rest is legal and law enforcement clients, along with a good number of small businesses.

The good news? I was able to save the company by following a few simple rules and my gut instincts. Even better news? These particular rules are applicable to any business in any industry:

1. Admit that failure is an option. One of the hardest things for a CEO to admit is that the product or innovation that launched the company may not be the one that sustains it long-term. It is hard to give up on the idea that launched 1,000 ships, but sometimes that idea can’t keep the ships afloat. Admitting that your business could go under if changes aren’t made is often a very difficult thing to do. But once you admit to yourself that the company is floundering, you have opened the line of thinking that is needed to eventually save your company.

2. Sometimes trial and error is necessary. Once you realize that your business needs to adapt to a changing market, you can begin to look for ways to save it. Though a scary proposition, sometimes trial and error is the only way to make any headway. If your tried-and-true radio advertising campaign suddenly isn’t bringing in new business, maybe it is time to try social media. If your current personnel aren’t bringing innovative products to the table, maybe it is time to bring in some new blood. When I realized it was time to make changes to my business, I tried various new methods of marketing, advertising, and hiring personnel. Some changes worked, others did not, but through the process I was able to streamline my business and utilize fresh techniques to get my company out of the red.

3. Realize that nothing will go as planned. Many times a CEO’s vision of growth and a profitable future can become the company’s Achilles heel. There are so many factors affecting various markets that are out of your control. That said, you have to be prepared to scrap visions and start fresh. When my company began to lose revenue, I had to figure out other sources of income aside from my medical clients. I focused on my bottom line. If you can’t pay your bills, you won’t be open for long. For every dollar or client lost, I looked for a creative solution to replace streams of revenue.

4. Listen to experts. If your company’s profits begin to head south, it is time to start listening. Focus on clients and what they are telling you, either verbally or with their wallets. Listen to media, other influencers in your market, and other businesses that share relationships with your clients. Find out where needs have shifted. Focus on communicating with your employees as best as possible. Often times your “feet on the ground” will have a better understanding of the pulse of the industry. Start asking questions and keep your ears open.

All businesses will reach a point where they need to diversify and adapt—or else face the possibility of failure. This rule applies to both the tiniest corner shop, as well as behemoths such as Apple and Google. Often, the simple acts of listening, observing, and trying new things can save a business from failure.

Photo credit: Shutterstock


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A Spider Weaves His Way Through the Art World

A Spider’s Heart is “a kid’s art book for adults. And vice versa.” In the words of creators, “it is about choosing a path that is right for oneself and not giving up. It is also about creativity and how it can help anyone solve any problem.”

If that weren’t enough to make me fall in love, the protagonist, Little Pablo (named after his grandfather, Little) is a vegetarian spider artist. His story begs the following questions: What happens when a spider refuses to kill other bugs? Will he starve to death? What about his urge to web, and how will art save him?

Written by Alon Seifert and illustrated by Eitan Cohen, the story is as beautiful and brilliant as the illustrations are.

Little Pablo webs art so major he lands himself a solo show at Bugosian Gallery and honestly, just thinking about him makes my heart swell.

The fact that we actually get a chance to meet Little Pablo in real life is like the chance to meet Kanye West before he turned into Yeezus. In other words: a once in a lifetime opportunity.

On June 2, Little Pablo will be making an appearance and signing autographs (or webbing them) at WeWork’s SoHo West space at 175 Varick Street from 10 a.m. to 6 p.m.

Seifert and Cohen will be creating Little Pablo’s art works in thread, creating a spiderweb-like 3D pieces on two large-size canvases. They will also project their animated film as well as the entire book, so people can flip through it.

I believe it is entirely possible that as Kanye has said of himself, this also applies to Little Pablo. “I am Warhol. I am the number one most impactful artist of our generation. I am Shakespeare in the flesh.”

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Get That Cool Job: Social Media Manager

Are you always wondering how people get those really cool jobs? Like a social media manager who gets paid to play on social media all day? With billions of people on Facebook, Twitter, and Instagram daily, we should all be getting rich, right?

But there’s a long list of specific skills needed to successfully manage a social media account. Savvy companies know that in order for an account to be beneficial to their business and brand, they have to hire a professional to get the results they want and save money and time in the long run.

First off, what does a social media manager do? A person with this job title (or a similar title, like social media strategist or social media coordinator) designs and administers a social media strategy that’s in line with a company’s brand.

What sort of experience do you need? According to Lia Zneimer, social media manager for WeWork, you don’t necessarily need a tech-heavy résumé.

“I think a variety of backgrounds can be helpful: communications, marketing, English (or whatever your native language is),” says Zneimer. “Millennials born into the digital age know it inside-out and use it in their daily lives, so in that regard, they’re building experience naturally. That said, I think solid writing skills can help, as can the ability to be resilient and think on your feet. I think social media is more about a natural skill set than it is about past experience. “

Those skills often include being a people person. Most individuals with this job love to meet and interact with people. It’s important, as they often spend hours each day interacting with customers and getting to know their client base.

Zneimer says that doesn’t necessarily mean all social media managers are extroverts.

“I think the kind of person who’s drawn to this job is someone who loves connectivity and relationships,” she says. “I don’t think social media managers necessarily have to be super outgoing; a quiet strength can help you in managing a social media channel. There’s lots of listening involved, lots of creativity, and lots of opportunity for meaningful one-on-one connections—all of which can appeal to those who aren’t extroverts by nature. “

The key word to the job title: personality. Be fun, outgoing, and have a sense of humor. You may think, “Hey, I’m behind a computer. Who can see my personality?” But people can see it in your words and interactions. They’ll be able to tell very quickly if you are a bore.

Knowing the right kind of content is key to being a great social media manager. You need to provide content that underscores the main points the company wants to get out there in the world. You will be writing across multiple platforms: blogs, Twitter, Facebook, Instagram, and any others your company decides is a valuable way to spread the word.

While everyone can post, tweet, or share a photo for their own benefit, not everyone knows how to utilize social media for a more general profit. This is where social media managers come in. Their job is to create a strategy for each social media handle and explain how each one can be beneficial to the growth of the company’s business.

Most companies will hire you based on your experience and results, rather than having a specific degree. Have a proven track record. Start with your personal account, and show that you can stand out.

“Develop your own social media presence, and make sure it’s up-to-date,” says Zneimer. “I’ve worked with social media managers before who don’t understand how Twitter works or who don’t have a LinkedIn profile of their own.”

Freshen up your skills by registering for classes on digital strategy, marketing, or social media. If you can contribute visuals for content posts, that’s a plus. And always look at what everyone else is doing.

“Familiarize yourself with all of the major platforms and create accounts on each,” says Zneimer. “Don’t be afraid to experiment. Start checking out the brands you admire and see what they’re doing on their social channels. Read voraciously—there are so many great resources out there. Even if you don’t have experience managing a corporate account, I think you can learn a lot from case studies.”

Photo credit: Lauren Kallen

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Working For Money Helps You Work

I couldn’t have been the only fan of Joseph Mitchell, the great New Yorker writer who died in 1996, at the age of 87, after not having published a word for the last 32 years of his life, who was hoping that a new biography would explain his long silence. The biography is now here—it’s called Man in Profile, and it’s by Thomas Kunkel—and I am sorry to say that I have no more insight than before into this famous case of writer’s block. The stakes are high, of course: I assume every writer, indeed every artist, lives with some ebbing and flowing terror that he will, at some point, be blocked, and become unable to write another word. Joseph Mitchell, he could be we.

But one of the subtle arguments of Kunkel’s biography is that it’s unfair to demand more productivity of Mitchell. After all, Up in the Old Hotel, Mitchell’s collection of masterful nonfiction from the years before he went silent, is 300,000 words long (for those of you who don’t think on word length, that’s a very fat novel’s worth, a Dickensian amount of words, or Dostoevskian). Who cares if it came mainly in his forties and fifties? We will always have the good stuff, collected in one handsome volume; an earlier volume, of Mitchell’s newspaper writings, is now back in print, too. I could re-read these books once a year and still not feel that I had read them enough.

But when Mitchell was alive, the fact that he was known to be alive, breathing and typing away, never finishing anything, was maddening. His fans were always waiting for the next story, waiting, the way I’m waiting for an R.E.M. reunion. Some things just don’t happen, and it’s best to stop wishing for them.


But the principal sufferer, the biography makes clear, was Mitchell himself. He never gave up hope of producing again, and he was angry and ashamed that he couldn’t. Which brings us to the question of “writer’s block”: some don’t think it exists, while others (especially those who have had it) consider it a disease on par with some milder forms of cancer.

One thing we can say is that it is more likely to afflict writers who aren’t badly in need of a paycheck. When one has to type to eat, one types. Much as I would like a trust fund, I am also aware that my relative poverty has been good for my productivity.

Mitchell was not rich, but he carried a different albatross: The New Yorker kept paying him, even as he was not producing. The magazine never paid him much, and in his prolific days, when he produced a work of genius every year or so, the magazine did not pay him enough. But it kept him on salary, and health insurance, through years lean and fat, even after it became clear that they were unlikely to get anything in return for their money.

Every writer I know would sell naming rights to her firstborn in exchange for a steady paycheck, not tied to the number of words produced. But Mitchell is our cautionary tale. The corporate dole can, for the wrong person, douse the fire. If New Yorker editor William Shawn had made Mitchell write in exchange for his money, perhaps the great master would have written again. Perhaps he would have been grateful. Maybe he was one of those artists—there are a lot of us—who need to need to work.

Photo credit: Therese Mitchell/The Mitchell Estate

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