Six Bold Predictions for Game of Thrones Season Six

If you aren’t caught up on HBO’s Game of Thrones yet, then I really don’t have much to say to you. Other than 1) go watch it, and 2) come back after to read this post. If you are caught up, then read on, because with just over two months to go, the time is right for some bold predictions.

1. Jon Is Resurrected by Melisandre

Carice van Houten as Melisandre – photo Helen Sloan/HBO

Carice van Houten as Melisandre – photo Helen Sloan/HBO

The red witch’s arrival at Castle Black was no mere coincidence. She shows up at the gate a defeated and broken woman, questioning her faith in the Lord of Light. Very shortly after her arrival, Jon Snow is stabbed and left for dead. Jon is a man with royal blood (more on that below below), and she is drawn to that like a moth to a flame.

With or without royal blood, one thing we know about priests and priestess of the Lord of Light is that they can resurrect people—even if their own faith is broken. Recall Season 3 when Thoros of Myr tells Arya  how he has resurrected Beric Dondarrion multiple times. Melisandre looked down on Thoros, thinking him less of a worthwhile servant of the light, and wondered how he came to behold such power from their religion. Now it’s her turn. A broken woman with shaken faith comes in to save Jon Snow.

2. Jon Snow is Royalty

This is more of a long-term prediction, as we might not get around to this reveal until later in the series. But, with Jon now resurrected and free of this bond to the Night’s Watch (“Night gathers, and now my watch begins. It shall not end until my death.”), his plotline opens up to the whole of Westeros. At some point his mother will be reveled, and my belief is that he’s the son of Prince Rhaegar Targaryen and Eddard’s sister Lyanna Stark. I’m not the only one to think this one may be possible.

3. Daenerys Wins Over the Dothraki

Emilia Clarke as Daenerys Targaryen – photo Macall B. Polay/HBO

Emilia Clarke as Daenerys Targaryen – photo Macall B. Polay/HBO

Let’s not speak about the unspeakable things that will probably happen to Dany as the Dothraki khalasar takes her captive. One thing that GoT is exceptionally good at is unspeakable crimes against humanity—especially against women. Yet here we are, in Season 6, hoping beyond hope that our favorite queen does not get harmed.

Regardless of what happens to her, the arc of her storyline seems to be about her conquering Essos piece by piece, in her quest to get back to Westeros.  After her capture, she’ll eventually win over this particular horde, uniting them and the cities of Slaver’s Bay under one rule: hers. A united Essos, plus a queen with dragons and designs on the iron throne means big battles in the next season.

4. Cersei Goes Berserk

Lena Headey as Cersei Lannister – photo Helen Sloan/HBO

Lena Headey as Cersei Lannister – photo Helen Sloan/HBO

And the start of Season 5 she was just an evil, power-hungry, scheming drunkard, by the end of it she was a broken woman with a glint in her eye that can only mean one thing: revenge. After her imprisonment and humiliation (shame… ding ding) Cersei’s world gets a lot smaller. Her uncle shows only contempt for her, her former sycophantic follower, Pycelle, returns the cold hatred she always showed him, and her son the king did nothing to save her. She still has to endure a trial at the hands of the High Sparrow, and to top it all off, Jamie returns with a dead Myrcella from what was supposed to be a rescue mission.

Her world, which previously revolved around power games and her children, has been stripped bare. There’s nothing left of her. She’ll go beyond simple cold-blooded revenge and sink deep into madness. A madness that will be executed by her new champion, the reincarnated Gregor Clegane and his creator, Qyburn. Look for Cersei to take it to a new level of insanity this season.

5. A Main Character Dies

Peter Dinklage as Tyrion Lannister and Conleth Hill as Varys – photo Macall B. Polay/HBO

Peter Dinklage as Tyrion Lannister and Conleth Hill as Varys – photo Macall B. Polay/HBO

Bold! I’m only half-joking. Of course lots of main characters get offed throughout the seasons, and usually in the most shocking ways possible. It’s not really a matter of someone dying, it’s a matter of whom and how many. My lovely wife—who makes a great Daenerys—has made the bold prediction that none other than, Daenerys herself gets killed this season. That’s bold.

I’m of the belief that Varis meets his maker. Someone has to die in the Essos storyline, and I like Tyrion too much and can’t bring myself to predict his demise—which actually makes him far more likely a candidate. That leaves Missandei, Grey Worm, and Varis. We’re starting to like Varis, which means he’s as good as dead this season. Maybe Tyrion and Varis both get killed. Maybe they kill each other!

6. Littlefinger Gets Hunted

We’ve watched the full series through twice, and it’s amazing to see the intrigue and subterfuge that Petyr Baelish weaves throughout the whole story. He is the architect of nearly all the conflict. Without his doing, Jon Arryn would not have died, Eddard Stark would have stayed in Winterfell, and the War of the Five Kings would have never taken place. And that’s just the start of his scheming. We might already hate him for marrying Sansa Stark off to Ramsay Bolton, but my prediction is that he gets found out in the show as the schemer that he is, and hunted down.

Bonus Prediction: Legolas Tracks Down Daenerys

“Not idly do the leaves of Lorien fall.”

When Dany dropped her ring at the end of Season 6, I couldn’t help but roll my eyes. Sure, it worked for Pippin and Merry, but it took an elf to spot the leaf. I don’t see any elves around, so the only logical conclusion is that Legolas, Prince of the Woodland Realm, arrives on the scene to find the dropped ring, and join the search. And if Legolas is there, that must mean that Essos is the actually the Undying Lands! Look for Elrond on the Small Council in Season 7. You heard it here first.

Why your startup team should always be pitching

Originally posted on the IBM Global Entrepreneur Blog on February 5, 2016.

Product. Team. Customers. Funding. The essential elements of a startup. But one more essential piece is missing: Pitch.

The Pitch is arguably the most important non-business piece of your startup. From your elevator pitch, to your public pitch, to your investor pitch, the more successful you are, the more integral these will become to your business and your life. Because of its importance, you should take absolutely every opportunity to pitch, especially in the early stages.


The first and biggest benefit from the always pitching mindset is practice. Don’t practice until you get it right, practice until you can’t get it wrong, is the modus operandi of true professionals in every walk of life. This needs to be your motto. Living room pitch practice only takes you so far; get out in front of the public and practice your pitch.

Now that you’re out in the public, you’ll benefit from the next most important thing: feedback. The Lean startup methodology is build, measure, learn. When you have built something, whether mockups, a fully functioning product, or anything in between, pitching becomes a part of the measure stage, and the feedback you receive is part of learning. This accelerates the Lean process for your startup, and gets you closer to product-market-fit, faster. Listen closely to the questions, and aggregate the feedback across many pitches to find the common threads. Use this to iterate for your next pitch and your next build.

Another benefit of always pitching is that you get to show lines not dots. The winner of IBM Smartcamp Boulder, Lawbooth, went on to win the regional and semi-final rounds of Smartcamp because they could show lines–progress and traction across a longer timeframe. The judges in Boulder had seen them pitch many times, and because of this, specifically commented on their growth over the past year. Being out in the community, pitching your startup over and over, while showing growth shows grit and dedication–two things investors love to see.

You can perfect your pitch through IBM SmartCamp and there are plenty of opportunities to pitch in your community too. You can look for some of the more common ones such as 1 Million Cups, events at startup weeks, or pitch competitions at local co-working spaces. Galvanize Pitches & Pitchers is one such example.

IBM’s Smartcamp is one part pitch competition, networking opportunity and a chance at competing for a spot in an incubator with investment in thirty cities globally. The top ten companies from this year’s competition got invited to LAUNCH Scale in October, and are soon to attend LAUNCH Festival in March. Along the way they got personal pitch coaching from one of the top angel investors in the world, Jason Calacanis, and had the opportunity to present in front of thousands of people at both LAUNCH Scale and soon, LAUNCH Festival.

If you’re interested in perfecting your pitch through IBM SmartCamp, you can click here to learn more about the program and enter your email address to receive details about the 2016 IBM SmartCamp.

Sales Primer for Non-Sales Startup Founders

Originally posted on the SoftLayer blog on January 27, 2016.

The founder of one of the startups in our Global Entrepreneur Program reached out to me this week. He is ready to start selling his company’s product, but he’s never done sales before.

Often, startups consist of a hacker and a hustler—where the tech person is the hacker and the non-tech person is the hustler. In the aforementioned company, there are three hackers. Despite the founder being deeply technical, he is the closest thing they have to a hustler. I’m sure he’ll do fine getting in front of customers, but the fact remains that he’s never done sales.

So where do you begin as a startup founder if you’ve never sold before?

Free vs. Paid
His business is B2B, focusing on car dealers. He’s worried about facing a few problems, including working with business owners who don’t normally work with startups. He wants to give the product away for free to a few customers to get some momentum, but is worried that after giving it away, he won’t be able to convert them to paying customers.

Getting that first customer is incredibly important, but there needs to be a value exchange. Giving products away for free presents two challenges:

  1. By giving something away, you devalue your product in the eyes of the customer.
  2. The customer has no skin in the game—no incentive to use it or try to make it work.

Occasionally, founders have a very close relationship with a potential customer (e.g., a former manager or a trusted ex-colleague) where they can be assured the product will get used. In those cases, it might be appropriate to give it away, but only for a defined time.

The goal is sales. Paying customers reduce burn and show traction.

Price your product, go to market, and start conversations. Be willing to negotiate to get that first sale. If you do feel strongly about giving it away for free, put milestones and limitations in place for how and when that customer will convert to paid. For example, agree to a three-month free trial that becomes a paid fee in the fourth month. Or tie specific milestones to the payment, such as delivering new product features or achieving objectives for the client.

Build Credibility
When putting a new product in the market, especially one in an industry not enamored with startups and where phrases like “beta access” will net you funny looks, it helps to build credibility. This can be done incrementally. If you don’t have customers, start with the conversations you’re having: “We’re currently in conversations with over a dozen companies.”

If you get asked about customers, don’t lie. Don’t even fudge it. I recommend being honest, and framing it by saying, “We’re deciding who we want to work with first. We want to find the right customer who is willing to work closely with us at the early stage. It’s the opportunity to have a deep impact on the future of the product. We’re building this for you, after all.”

When you have interest and are in negotiations, you can then mention to other prospective customers that you’re in negotiations with several companies. Be respectful of the companies you’re in negotiations with; I wouldn’t recommend mentioning names unless you have explicit permission to do so.

As you gain customers, get their permission to put them on your website. Get quotes from them about the product, and put those on your site and marketing materials. You can even put these in your sales contracts.

Following this method, you can build credibility in the market, show outside interest in your product, and maintain an ethical standing.

Get to No
A common phrase when I was first learning to sell was, “get to the ‘no’.” It has a double meaning: expect that someone is going to say “no” so be ready for it, and keep asking until you get a “no.” For example, if “Are you interested in my product?” gets you a “yes,” then ask, “Would you like to sign up today?”

When you get to no, the next step is to uncover why they said no. At this point, you’re not selling; you’re just trying to understand why the person you’re talking to is saying no. It could be they don’t have the decision-making authority, they don’t have the budget, they need to see more, or the product is missing something important. The point is, you don’t know, and your goal here is to get to the next step in their process. And you don’t know what that is unless you ask.

Interested in learning more? Dharmesh Shah, co-founder and CTO of Hubspot and creator of the community OnStartups, authored a post with 10 Ideas For Those Critical Early Startup Sales that is well worth reading.

As a founder, you’re the most passionate person about your business and therefore the most qualified to get out and sell. You don’t have to be “salesy” to sell; you just need to get out and start conversations.

A Brief Critique of The Force Awakens

Taking a break from the Startup Series reposts to put down my thoughts on Star Wars Episode VII: The Force Awakens. And yes, major #SpoilerAlert ahead, but if you haven’t seen TFA yet, I have no sympathy for you. Heck, if you haven’t seen it twice by now, I’m questioning your place in my life.

First, the good. I absolutely loved it. It was part fan tribute, part sci-fi action flick, part story continuation, and part stage-setting for new stories in our favorite galaxy. One of the best moments of the whole film is when you see the Millennium Falcon for the first time. Absolutely awesome. And though the entire final sequence of the movie is basically a rehash of RotJ, I didn’t care.


One of the best surprises was that Rey was the awakening. The trailers led me (and many others) to believe that Finn was the new Jedi. They show him holding a lightsaber, and who holds lightsabers? Jedi, that’s who. Ergo: Finn = Jedi. When it turned out that Rey was the force-sensitive, and rapidly learned how to tap into her powers, I was stoked. I absolutely loved that. Good job on the trailer red herring.

However, there were moments that took me out of movie-adoration mode. It’s no fun to be pulled out of suspension of disbelief, especially because I’ve been anxiously anticipating it, and secretly praying every night for a great movie since it was announced on October 30, 2012. Thankfully, the instances of being pulled from excitement and awe in Episode VII were far less than any 20 minute segment of any of the prequels, but there were still a few moments that left me shaking my head.

Starkiller Base on The Force Awakens movie poster

Another Death Star

Really? Another Death Star? Come on. When they revealed Starkiller Base, my first reaction was the mental equivalent of an eyeroll.  Seven movies and three Death Stars? That’s a bit much. And I must admit that I saw it coming because it is in the movie poster. Even with that, I didn’t think they’d ever possibly revisit the idea of a Death Star a third time. But they did. This plot device (pun intended) needs to be put to rest, once and for all.


Captain Phasma Caves

While the whole scene with Phasma, Finn, Han, and Chewie was funny—from capture to the trash compactor—the fact that she caved and turned off the deflector shields was just too much bullshit for me. This is the Chrometropper who is so unquestioningly loyal that when a Stormtrooper does not participate in mass-murder of unarmed civilians, she censures them and sends them to reconditioning. And you mean to tell me she begrudgingly gives in just because she has a blaster pointed to her head? I’m not buying it. Not to mention the minor details that she a) knows how to turn off the deflector shield of an entire planet, b) has the authority to do so, and c) happens to be in the right place for it. <sigh>

"all out" assault on Starkiller base


The All-Out Assault

Picture this: the Resistance is backed up against a wall. Their senate—and the moon system surrounding it—was destroyed by a “hyper-lightspeed” weapon of unbelievable firepower. And that weapon is turning its attention to their primary command base. Their only chance to survive: a zany scheme that took about five seconds to concoct (though, admittedly, they’ve already pulled off this plan twice before, which must certainly add a degree of confidence). But it is their own chance to survive; the one and only way to save the entire Resistance armed forces! What do you do? Meh, send about a dozen X-Wings, into enemy territory, to attack a planet-sized based. That should be plenty.  You mean to tell me that with absolutely everything on the line, you can’t muster more than a couple of single-seaters? Even the Rebellion did better in RotJ.


Even with those missteps, I still loved it. My wife and I are heading for our third viewing this Saturday.

Oh, and, Kylo Ren as Han & Leia’s son? I totally called it. #humblebrag But to keep myself honest, I also speculated that Rey was their daughter, and though that is as-of-yet unproven, I’m saying “no” on that one.

Startups should embrace both diversity and inclusion

Originally posted on the SoftLayer blog on December 9, 2015

During the NewCo Boulder festival, web development agency Quick Left gave a talk about diversity and inclusion in the workplace. The panelists shared stories of their experiences around diversity—good and bad—and gave advice on what can be done to make workplaces more inclusive. It was one of the best talks I heard all year.

After much discussion, both philosophical and tactical, an audience member expressed concern about counter-discrimination. Would the time come when he would be overlooked for a job because he was not a diversity candidate?

This is not the first time this has been brought up in diversity discussions, and he was expressing what many (perhaps too many) straight white males think when diversity is discussed. To the credit of Gerry Valentine, one of the panelists, he did not chastise the audience member, and instead commended him for his bravery. The man who asked the question gave voice to a common concern that is often thought, but rarely brought up. The panelists at NewCo Boulder handled it very well, pointing out that no one wants a job just based on their gender, skin color, sexual preference, or anything other than their ability to execute on the job. And, collectively, we want to create a world where everyone has the opportunity to compete for jobs on equal ground.

I was truly moved by the entire session, but found myself upset that even at the close of 2015 we are still answering questions about counter-discrimination. When Gerry commended the question for its bravery, I first wondered if he was being glib. But knowing Gerry, I was certain he was serious about his comment. Upon further reflection, I realized what’s interesting about this “pale and male” pushback is that it comes from a place of fear. A fear of discrimination is at the root of the question when someone asks, “As a white male, am I going to get passed over for a job because this company wants to hire for diversity?”

Following Gerry’s example, it’s OK to acknowledge that fear. It’s OK to point out that white men don’t want to live in a world where they are discriminated against, even subtly. While that is a valid fear, for the straight white male candidate, it is only a fear of a potential future. If they can imagine potential discrimination, can they acknowledge that the reality of our world today: anyone who isn’t a straight white male does experience this as real fear. Imagine walking into a job interview having to first overcome the things about you that you cannot control (gender, skin color, sexual orientation, physical handicap, economic background, country of origin, etc.) just to get to a level playing field with the other candidates. If you don’t want this for yourself, you certainly wouldn’t want it for anyone else.

In startups, we love to talk about unfair advantage, but when it comes to hiring, the only unfair advantages should be skills and experience. What the movement for inclusion and diversity is about—and what we should be striving for—is a world where we all compete equally. If it is a brave thing to express your fear publicly, it is braver still to acknowledge the reality of the situation and work to rectify it.

One of the things I love about the startup community is that once we identify a problem, we move forward to solve it in as many ways possible. The path to inclusion in the workplace doesn’t have to be a pendulum that oscillates between two extremes—discrimination and counter-discrimination—before settling down in the middle. Pendulums are a relic of the industrial era. In the digital era, we can choose our target, set our standards, and move forward as a community to achieve them. As you build your startup, build inclusion in your workplace from day one.

The Dumbest Thing I’ve Ever Said

Originally published on the SoftLayer Blog on October 21, 2015

Last week, I attended the LAUNCH Scale conference and had the pleasure of attending the VIP dinner the night before the event began. We hosted the top 10 startups from the IBM SmartCamp worldwide competition for the dinner and throughout the events. Famed Internet entrepreneur Jason Calacanis joined us for the dinner and gave a quick pep talk to the teams. He mentioned that people come up to him and lament that they wished they’d gotten into the “Internet thing” earlier—and that he’s been hearing this since 1999. His story reminded me of a similar personal experience.

In the fall semester of 1995, I was a junior at St. Bonaventure University, working in the computer lab. One day after helping a cute girl I had a crush on, she said to me, “You’re so good with computers, why aren’t you a computer science major?” Swelling with pride, I tried to sound impressive and intelligent as I definitively stated, “Windows 95 just came out, and pretty much everything that can be built with computers has been built.”

Yep. Windows 95. The pinnacle of software achievement.

It is easily the dumbest thing I’ve ever said—and perhaps up there as one of the dumbest things anyone has said. Ever.

But I hear corollaries to this fairly often, both in and outside the startup world. “There’s no room for innovation there,” or “You can’t make money there,” or “That sector is awful, don’t bother.” I’m guilty of a few of those statements myself—yet businesses find a way. We live in an age of unprecedented innovation. Just because one person didn’t have the key to unlock it doesn’t mean the door is closed.

Catch yourself before you fall into this loop of thinking. It might mean being the “Uber of X” or starting a business that’s far ahead of its time. Think it’s crazy to say everything that can be built has been built? I think it’s just as crazy to say, “It’s too late to get into ___ market.”

For example, when markets grow in size, they also grow in complexity. The first mover in the space defines the market, catches the innovators and early adopters, and builds the bridge over the chasm to the early and late majority. (For more on this, read Crossing the Chasm by Geoffrey Moore.) When a market begins to service the majority, the needs of many are not being met, which leaves room for new entrants to build a business that addresses the segments dissatisfied with the current offerings or needing specialized versions.

The LAUNCH Scale event showcased dozens of startups and the innovation out there in the world always amazes me. I’d recommend it to any startup that has built something great, and now needs to scale. Still haven’t built something yourself? Think you missed the opportunity to build and create? In 1995, I didn’t think about how things would change in five, 10, even 20 years. Now it’s 2015 and the startup world has been growing faster than any sector in history.

Think everything that could be built has been built? Think again. Want to build something? Do it. Build something. What are you waiting for? Go make a difference in the world.

Free Resources for Your Startup

Originally published on the SoftLayer Blog on August 25, 2015.

Building and running a startup is both difficult and expensive. From salary to servers to services, the demands on your budget are constant and come from all directions. On the Catalyst team we know this firsthand—our program was created as a way for startups to access SoftLayer’s robust platform before they have revenue or funding.

After moving to Boulder, Colorado in 2012, the first startup I joined was a member of the Catalyst program. Without Catalyst, our organization would have been paying out of pocket for the bare metal servers we needed. Instead, that money was freed up for other essentials (like food to keep us alive).

Infrastructure isn’t the only area in which startups can leverage free offerings. Since joining the Catalyst team one year ago, I’ve tracked and collected other free resources for startups. I compiled my research into a presentation that I’ve given at a few events. The presentation is available on SlideBean(a free online presentation platform, what else?) and is constantly being updated. Some highlights are below:

Big Company Programs
The Catalyst program is a model on how big companies can meaningfully engage with startups, and we’re not the only ones doing it.

  • SVB: Silicon Valley Bank offers a program called Accelerator. Perks including free checking and financial mentorship. While saving on business checking won’t make a big dent in your cash flow, the financial mentorship is top notch. The SVB team consists of experts in banking who can offer advice on fundraising, financial instruments, and cash management.
  • SendGrid: Email deliverability is crucial for your company, so start with the best in the business. The free plan includes 10,000 emails per month, up from 200 emails per day when I first started giving this talk. Go to the pricing page and scroll down to the bottom for the free plan. (Full disclosure: SendGrid is a former partner.)
  • NASDAQ Exact Equity: I was recently at a VC conference, where I had two separate conversations about investors’ frustrations with disorganized or downright undocumented cap tables. The NASDAQ Exact Equity freemium tool will not only help you wrangle your cap table, but it will also signal success to the investor by showing that you’re thorough and organized.

Startup Freebies
I’m not going to cover the basics, such as Evernote, Trello, Asana, Pivotal Tracker, Launch Rock, Bootstrap, Google Drive, etc. You probably already know about these programs. Instead, I’ll share a few great ones you may not know about.

  • Docracy: If you need any sort of legal document, Docracy should be your first stop. The legal documents were prepared by lawyers and are available for free. The choices range from SaaS Terms & Conditions to founder agreements.
  • HTML5 UP: Need a quick, easy, and responsive template for your site? When WordPress is too much of a hassle for a splash page, head over to HTML5 UP for dozens of choices of free templates.
  • UI Kit: As you’re moving from the free HTML5 UP template toward being able to build out your site with the free Bootstrap toolkit, save yourself coding time and get the UI Kit for free design elements such as lightbox, slider, accordions, and more.
  • SlideBean: I love SlideBean. While searching for “free PowerPoint templates,” I discovered that all the templates were hideous. Then I stumbled across SlideBean and fell in love with it. It makes putting together a presentation quick and easy, and keeps it from looking like you traveled to 1999 to get your template.

Below are my favorite collections of resources for any freebies that I haven’t already covered.

  • Product Hunt List: The founder of CrazyEgg and KISSmetics has an exhaustive list of free and freemium products for your startup.
  • Over 400 resources are grouped by category. I especially love the design resources.
  • Startup Stash: Not all of the free deals, mostly in the form of percentage discounts. But if you’re going to pay for something, check F6S first for a discount.

And finally, the best piece of advice when trying to save money can be found in my last post: A Grandmother’s Advice for Startups: You never know ‘til you ask.

Have a free resource that you absolutely love that’s missing from my list? Email me or tweet me @stoneybaby and let me know!


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

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

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

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.