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A Grandmother’s Advice for Startups: You Never Know Unless You Ask

By Life

Originally posted on the SoftLayer Blog on April 17, 2015.

Today my grandmother turns 95. She’s in amazing shape for someone who’s nearly a century old. She drives herself around, does her own grocery shopping, and still goes to the beauty parlor every other week to get her hair set.

Growing up less than a mile from her and my granddad, we spent a lot of time with them over the years. Of all of the support, comfort, and wisdom they imparted to me over that time, one piece of advice from my grandmother has stood the test of time. No matter where I was in the world, or what I was doing, it has been relevant and helpful. That advice is:

You never know ‘til you ask.

Simple and powerful, it has guided me throughout my life. Here are some ways you can put this to work for you.

Ask for the Introduction
Whether you’re fundraising, hiring, selling, or just looking for feedback, you need to expand your network to reach the right people. The best way to do this is through strategic introductions. In theCatalyst program, making connections is part of our offering to companies. Introductions are such a regular part of my work in the startup community. In my experience, people want to help other people, so as long as you’re not taking advantage of it, ask for introductions. You’re likely to get a nice warm introduction, which can lead to a meeting.

Ask for the Meeting
Now that you have that introduction, ask for a meeting with a purpose in mind. Even if you don’t have an introduction, many people in the startup world are approachable with a cold email.

Guy Kawasaki, former chief evangelist for Apple, and author of 13 books including The Art of the Start 2.0, wrote a fantastic post, “The Effective Emailer,” on how to craft that all-important message with your ask.

Another great take on the email ask is from venture capitalist Brad Feld, “If You Want a Response, Ask Specific Questions.” This post offers advice on how not to approach someone. The title of the post says it all, if you want a response, ask a specific question.

Ask for the Sale
Many startup founders don’t have sales experience and so often miss this incredibly simple, yet incredibly important part of sales: asking for the sale. Even in mass-market B2C businesses, you’ll be surprised how easy and effective it is to ask people to sign up. Your first sales will be high-touch and likely require a big time investment from your team. But all of that work will go to waste if you don’t say, “Will you sign up to be our customer?” And if the answer is a no, then ask, “What are the next steps for working with you?”

Empower Yourself
It’s empowering to ask for something that you want. This is the heart of my grandmother’s advice. She is and has always been an empowered woman. I believe a big part of that came from not being afraid to ask for what she wanted. As long as you’re polite and respectful in your approach, step up and ask.

The opposite of this is to meekly watch the world go by. If you do not ask, it will sweep you away on other people’s directions. This is the path to failure as an entrepreneur.

The way to empower yourself in this world starts with asking for what you want. Whether it’s something as simple as asking for a special order at a restaurant or as big as asking for an investment, make that ask. After all, you’ll never know unless you ask.

Startups: Always Be Hiring

By Everything

Originally posted on the SoftLayer Blog on March 20. 2015.

In late 2014, I was at a Denver job fair promoting an event I was organizing, NewCo Boulder. All the usual suspects of the Colorado tech community were there; companies ranging in size from 50 to 500 employees. It’s a challenge to stand out from the crowd when vying for the best talent in this competitive job market, so the companies had pop-up banners, posters, swag of every kind on the table, and swarms of teams clad in company t-shirts to talk to everyone who walked by.

Nestled amid the dizzying display of logos was MediaNest, a three-person, pre-funding startup in the Catalyst program, at the time they were in the Boomtown Boulder fall 2014 cohort. What the heck was a scrappy startup doing among the top Colorado tech companies? In a word: hiring.

MediaNest was there to hire for three roles: front end developer, back end developer, and sales representative. They were there to double the size of their team … when they had the money. In the war for talent, they started early and were doing it right.

I’ve often heard VCs (venture capitalists) and highly successful startup CEOs say the primary roles for a startup CEO are to always keep money in the bank and butts in seats. Both take tremendous time and energy, and they go hand-in-hand. It takes months to close a funding round, and similarly, it takes months to fill roles with the right people. If you’re just getting started with hiring once that money is in the bank, you’re starting from a deficit, burning capital, and straining resources while you get the recruiting gears going.

The number one resource for startup hiring is personal networks. Start with your friends and acquaintances and let everyone know you’re looking to fill specific roles, even as you’re out raising the capital to pay them. As the round gets closer to closing, intensify your efforts and expand your reach.

But what happens if you find someone perfect before you’re ready to hire them? Julien Khaleghy, CEO of MediaNest, says, “It’s a tricky question. We will tend to be generous on the equity portion and conservative on the salary portion. If a comfortable salary is a requirement for the person, we will lock them for our next round of funding.”

MediaNest wasn’t funded when I saw them in Denver, and they weren’t ready to make offers, so why attend a job fair? Khaleghy adds, based on his experience as CEO, “It’s actually a good thing to show a letter of intent to hire someone when you are raising money.”

At that job fair in Denver, MediaNest, with its simple table and two of the co-founders present, was just as busy that day as the companies with a full complement of staff giving away every piece of imaginable swag. I recommend following their example and getting ahead of the hiring game.

As long as you’re successful, you’ll never stop hiring. So start today.

To Raise Capital You Need a Startup Roadshow

By Everything

Originally published on the Softlayer Blog on February 25, 2015.

In the world of big finance, before a company IPOs, the CEO along with an investment banker(s) go on a global roadshow to pitch their business to potential investors, including hedge funds, major investment funds, and other portfolio managers. The purpose is simple: Drum up sales of the forthcoming stock issue. In the startup world, there are no big investment banks scheduling meetings. However, there are opportunities to do a roadshow for your startup, which is even more important than the IPO.

There were 275 IPOs in 2014, the largest number since 2000. By contrast, there are around 500,000 new businesses founded in the U.S. each year (not all of which are tech startups), approximately 225,000 angel investors in the U.S., and as of a year ago, there were 874 venture capital firms [read more]. In big finance, a few companies compete for the attention of a small, accessible group of investors. In the startup world, a large number of companies must seek capital from a huge pool of often-hard-to-find, geographically dispersed investors. Because of this, a roadshow is even more important for startups than it is for IPOs.

The SoftLayer Catalyst team works with startups in communities as big as San Francisco’s Silicon Valley to as small as Cedar Rapids, Iowa. The number one thing entrepreneurs outside of the major financing hubs ask about is how to access capital. My response is always the same: Your job isn’t to bring more capital to your local community; it’s to build a great company. You know where the capital is, so build something worth investing in, and then do a roadshow.

Practice Locally

Thankfully, as the startup world grows & matures, the number of outlets for pitching increases every month. There are opportunities in most cities to stand up and pitch your idea to your peers or investors. Start by getting out in front of your local community as often as possible. In the Boulder/Denver community, there are a few companies that I see pitch all the time, and those companies have fantastic pitches because they are constantly practicing, getting feedback, and refining.

Look for meetups that focus on pitching such as 1 Million Cups and House of Genius, or simply do a search for startup pitch meetup in your city. During startup weeks or similar events, search and sign up for pitch practices and competitions. If your co-working space is like SoftLayer partner Galvanize, they might have a big member pitch competition or a peer-to-peer practice event. Participate in as many local and regional pitch competitions as you can find. As long as the competitions don’t take a piece of equity or require a significant payment to participate—either of which should be very carefully evaluated beforehand—sign up, and compete. This constant exposure to your local market will help spread the word about your company, provide feedback on your pitch, and maybe even score some prizes!

For more advice on your pitch, read my previous post, Advice from the Catalyst Team: Pitching Like George Lucas.

Maximizing Your Startup Roadshow

Now that you’ve refined your pitch and practiced in front of as many local audiences as possible, it’s time to start planning your roadshow. Traveling on a limited budget means you must plan a highly focused trip with a specific goal in mind. Maybe you’re traveling from New York City to Philadelphia for a competition, or from Portland to San Francisco for an investor meeting; no matter the reason, it’s imperative to maximize your trip. A good roadshow involves getting the absolute most out of your travel budget, and this means booking meetings with potential investors or customers.

For example, while attending StartSLC, I visited with a friend from Colorado, Ryan Angilly fromRamen. Angilly traveled to Salt Lake City to participate in the pitch competition, but he made the most out of his trip by filling his calendar with investor meetings throughout the week. Before his trip, he reached out to his contacts in the startup community in Utah and asked for introductions. After following through with the contacts, he met with investors he would have otherwise never met.

Start by either allocating a budget for travel or identifying the most important pitch competitions in your region or industry. Once you have your trip scheduled, immediately start looking for connections within your network. It’s far more effective to say, “I’ll be in town the 12th to the 14th; what does your schedule look like?” than a non-specific request such as, “When are you available?” Look for connections with ties to your local community as they are more likely to be helpful and make intros on your behalf. And ask around locally about who has ties to your destination. Get your meetings lined up, and get ready for a whirlwind of pitches on your first ever startup roadshow.

I’ll leave you with this final point: In 2014, venture capital firms raised nearly $33 billion, a 62 percent increase over 2013 levels. They’ll spend the next few years investing that money in startups. The money is out there, and you need to do a roadshow to find it.

Advice from the Catalyst Team: Pitching Like George Lucas

By Everything

Originally posted on the Softlayer Blog on December 4, 2014.

SoftLayer’s Catalyst team hears startup pitches constantly.

We support more than 50 accelerator programs in the Global Accelerator Network, theTechStars programs, five hundred startups, and more. We hold office hours, offer pitch practice, and attend demo days—in short, we hear a lot of pitches.

Condensing the essence of how you’re changing the world into a five minute sales pitch, while still including other key elements like the business model, traction, early wins, team, and “the ask” is incredibly difficult. There’s a lot of ground to cover and very little time to do it, especially when you consider that likely half of your audience is focused on their phones.

A pitch must be concise, informative, and attention grabbing. The worst thing you can do is pitch like George Lucas’ dialogue in the Star Wars  prequel trilogy movies—clumsy and over-explaining.

Yoda: Always two there are, no more, no less, a master and an apprentice.Mace Windu: But which was destroyed, the master or the apprentice?

This particular quote is the epitome of terrible dialogue because it communicates the same thing multiple times; the second line is superfluous. I don’t need Mace Windu to re-explain to me exactly what Yoda just said. I have ears. I’m paying attention. Imagine how much more powerful that scene would be with just the first statement.

Most of us have a natural tendency to over-explain a point, but by doing this, we insult the intelligence of our audience. Plus, over-explaining eats up precious time and causes the crowd to disengage. I can’t think of a worse combination.

If you find yourself saying any of these phrases, cut them immediately:

Let me show you . . .
I’d like to tell you . . .
I’m going to . . .
I think . . .
For example . . .
As I said before . . .

Simply put, don’t tell me you’re going to tell me something. Just tell me.

George Lucas did write some great lines of dialogue. Watch the Dagobah scenes in Empire Strikes Back. Yoda’s lines are pure brilliance. The message is simple and powerful, which makes it one of the most memorable lines in cinema.

“Do or do not. There is no try.”

During a pitch, you’re not writing a screenplay, so you don’t want to leave your audience guessing, but you still need to explain the problem, the solution, and why you’re the best at solving it. Don’t leave your audience confused from a lack of information, but don’t insult their intelligence by telling them you’re going to tell them something. Just tell it. Or better yet, show it.

You want your pitch to be like a Lightsaber: an elegant weapon for a more civilized age.

5 Basic Rules for Startups at Expos

By Everything

Not NY Tech Day. But definitely NY.

Last week I happened to be in New York City while the second annual NY Tech Day was taking place. It was an expo of hundreds of NYC-based startups showing off their companies and products. For my fellow Boulderites, think of BoulderBeta, but 50 times larger, and without beer. And in New York. So I guess it was nothing like BoulderBeta, except that it had tech companies showcasing their products.

It ended up being very productive for me on a number of fronts. However, the biggest takeaway for me was not any one particular company, but an observation of how the exhibitors set up their tables and worked the crowd.

I’ve been to big, flashy, expensive trade shows all over the world, where every exhibitor been doing tradeshows for years, or has been attending for years before their first time exhibiting. In those environments, everyone has the basics down, so the exhibitors go to great lengths to stand out from the crowd. NY Tech Day was very different; it seemed few of the companies had experience at trade shows, and did not have an understand of the basics for exhibiting. If I ever end up showcasing a company at an expo such as that, I’ll follow these guidelines:

1. Use your tagline on your banner

Your logo is great. Really, it is. I love it. But unless your logo spells out what your company does in one succinct sentence, then you need to add your tagline to your banners. Unless of course your tagline doesn’t spell out what your company does in one succinct sentence, in which case, you need to take a day to rework your tagline until it does. And then add it to your banner.

2. Put your tagline at eyelevel or above

Now that you have your tagline on your banner and promotional materials, don’t just hang it off the front edge of your table where it’s blocked by everyone’s legs and completely unreadable. Buy a pop-up banner, or hang your banner up above your table, do something–anything–that gets your logo (because you love your logo) and tagline where everyone can see it.

3. Have more than one person

Working a booth at an expo is a long, tiring job. And it’s far, far worse when you have to work it yourself. But more importantly, you can only talk to one or two people at a time in a crowded, noisy convention hall. Realistically, each person you talk to about your company has a different need, and you need to tailor your pitch to each of them individually. So while you’re talking to the one guy with a small use-case that’s not exactly the right product fit, the woman who is your ideal client just grabbed a flyer from your table, probably never to call you again.

Have your partner there. Have your staff there. Have as many people there as you can fit, and rotate shifts so no one person gets exhausted. If you’re flying solo—which every book on entrepreneurship will tell you is a bad idea—then ask friends to come and help you. Even if it’s you and your partner, still ask a few friends to come and help, you’ll be glad you have the support.

4. ABP – Always Be Pimpin

You know that logo we all love so much? Wear it! You know those friends you invited to come and help you out? Get them wearing it. Get t-shirts for every single person at your table. Everyone at your booth should be branded. Also, make sure you have some sort of takeaway, either business cards or flyers. And make sure they are not glossy on one side, so your booth visitors can jot down notes about how incredible your company is. Before it gets lost in their bag of other flyers.

5. Stand up & engage (but don’t harass)

You’d think this would be Expo 101. You’d think that, and you’d be wrong. I saw at least a dozen tables where the exhibitors were sitting down, behind the table, staring at their phone. Being an entrepreneur is hard, and you’re constantly pulled in a million directions. I get it. But if you’ve paid to be at an expo, then you best be expo-ing. Stand up, come around in front of your table, put your phone away, and engage people.

Of course, don’t take it to the opposite extreme. There was one booth with guys using aggressive sales tactics, trying everything from guilt to shame to false flattery to get people to listen to their pitch and sign up for whatever it was they were schlepping. That doesn’t fly in the startup world, not even in the NYC startup scene.

Advice for the attendees

Lastly, I have one bit of advice for attendees, stop and talk to as many people as your schedule allows. My friend, Eric Schwertzel of Booshaka, broke all of these rules, except #5. Yet despite his poor showing (sorry Eric, I got nothing but love for ya!) you wouldn’t know he’s one of the best in the biz at signing major media contracts for startups all over the world.

If you’re wandering the floor, stop and talk because you never know what you might discover. In startups, as in NYC,  “you gotta be willing to be lucky.” (quote from Al Pacino’s character in City Hall.)