Thankful for Specialist Rorey McFarland

I led a battalion reconnaissance platoon during a fifteen month deployment to Iraq back in 2006 - 2007. Specialist Rorey “Mac” McFarland served as the company armorer. He was responsible for ensuring that all of the weapons in the company were properly tracked. The position was ironic, for Mac had lost his weapon just after he first reported to the unit in late 2005. And because losing your weapon is a good way to get on the wrong side of the Battalion Command Sergeant Major, Mac found himself banished to the company arms room. 

I had just taken over the recon platoon when Mac got in trouble. The initial punishment seemed to fit the offense but as time wore on I started to pity him. Mac was unfailingly polite and respectful whenever I dealt with him, and, despite the fact that he wasn’t part of a platoon, he kept a positive attitude towards his job and the unit leadership. During the thirteenth month of our combat tour, after Mac had spent nearly eighteen months as the company armorer, I went to the company commander and asked him to let Mac join my platoon. My reasoning was simple. As an Infantryman, I had no idea what I would tell my family and friends if I returned from a fifteen month deployment to Iraq without ever having participated on a combat patrol. So I asked the commander to let Mac join my handpicked  platoon for the two remaining months of our combat deployment, if only as a driver.

To my surprise and the company commander’s credit, he agreed to let Mac join my platoon. I’ll never forget the smile that creased his face from ear to ear when he found out that he was part of a platoon, a team, for the first time. Later, one of my sergeants told me that Mac had called his family and told them: “I’m a battalion scout now.” Mac told that sergeant it was the first time he had ever been proud to tell his family what he did in the Army. 

A few days later, we were driving down a major highway in western Baghdad called Route Irish to conduct a patrol in a nasty neighborhood in central Baghdad named Dora. Our battalion had sustained a high number of casualties pushing into parts of Dora where Americans had not maintained a meaningful presence for at least two years, so we were reflective as we left the relatively safe confines of the base for the insurgent infested neighborhood.

Quietly, over the internal intercom, one of my soldiers asked a simple question: “What do you guys think about dying over here?”

I’ll never forget what happened next. Mac responded without hesitation. He said, “You know, I don’t mind if I die over here. Because if I die over here people will always remember that I gave my life for something bigger than myself. People will always look at your sacrifice over here in a different way.” I tried to talk but suddenly, unexpectedly, I found that I had choked up.

Mac was 22 years old at the time. Today, I am thankful for him and for all of the brave and selfless men and women who keep us free. 

So I know you probably know I am a military spouse! Well to all my fellow military spouses out there, I wanted to know if yall heard of something called Troopswap???? It’s a site that gives us discounts and more you just have to make a free account and enjoy the benefits. You can get disounts from everything like Under Armour to So I wanted to make sure yall knew about this site too!! Enjoy!!

Paralyzed Veteran Fighting For VA Benefits

An Army buddy shared this moving story with me and I felt compelled to share it. Former Army Medic Jeremy Smith was wounded and paralyzed in Afghanistan. Upon applying for VA benefits, he was told by a counselor that he “wasn’t disabled enough.” Understandably shocked (he is paralyzed from the waist down) he retorted, “How can I not be disabled enough? How much more disabled do I need to be? Do I need to go throw myself under a bus real quick?”

Watch his story on CBS News here.

George Washington believed that America’s treatment of her veterans directly correlated with her ability to fight and win future wars.

The willingness with which our young people are likely to serve in any war, no matter how justified, shall be directly proportional to how they perceive the Veterans of earlier wars were treated and appreciated by their nation.”

One day, I hope that achieves enough scale that we can provide the funding via the Wounded Warrior Project to take care of veterans like Jeremy who are falling through the cracks. I can only imagine the bitterness of a veteran who has given up his right to walk in order to defend the freedom of the very counselor who treats him with such disdain. If his situation is not rectified, it will form a permanent blight on America’s honor.

TechStars NYC on Bloomberg TV

A new Bloomberg TV series charts the trials and tribulations of tech entrepreneurs participating in the most elite tech incubator program in New York City: TechStars. David Tisch, the Managing Director of TechStars NYC, is a TroopSwap seed investor and advisor. He gave us the early runway and advice we needed to make our site a reality. If not for him, the TroopSwap team wouldn’t have been able to pursue our mission of serving the military by bringing military discounts to the web. You can check out the show here: To Launch Military Discounts in San Diego and Washington D.C.

After months of hard work, we are proud to announce that tomorrow, October 4th, we will be launching online military discounts on in two new markets: Washington DC and San Diego. KPBS News is helping us spread the word to members of the military community in San Diego:

5 Essential Keys to Startup Success

After twenty-four months of running my own startup, I’ve decided to take a few moments to reflect on the things I wish I knew before I started down this path. After closing a 2.5M financing round, I think it’s important to reflect on what I have learned over the last two years. After all, taking a startup from the idea phase to an actual company with employees that is generating revenue is a difficult task that will require years of your life, keep you up for many late nights and, typically, will add a few extra pounds to your waistline. Despite the wide ranging challenges you will face while building your company, I have found that starting a company is very similar to writing a cohesive essay. In order to make an impact with your company or to create literature, you will need to: define your problem, understand your audience, find a mentor, find the right partner, and you will have to be product driven early on.

Define Your Problem

The most essential thing you need to do is to identify a real problem. Ultimately, everything you do will be focused on solving and monetizing that problem so you had better pick a serious problem that affects a lot of people. I’ve noticed that many fellow entrepreneurs fall into one of three camps. The first camp is full of people who think other people are like them too. A good example of this entrepreneur is your friend who is crazy about fantasy football and who wants to start a group based messenging service for draft day. The problem is that this business isn’t a business at all — it’s an incremental feature for ESPN or Yahoo!. This market is limited to sports nuts who will only use the feature once a year, or, if they use it for gamedays too, then for a maximum of 15 odd days per year. The infrequency of need means that it will be very difficult to create habits that will addict your users to your product. The second camp is full of entrepreneurs who have identified a real problem but who haven’t identified a defensible solution that solves that problem in a way that is substantially different from competitors. Typically, the entrepreneurs who fall into this camp have identified a real need but don’t have the industry knowledge or connections — “the unfair advantage” — that would allow them to disrupt the industry. The third camp of entrepreneurs have identified a real problem and they have a truly unique solution to that problem BUT… their business lacks defensibility so incumbents with more resources can effectively enter the space and quash them before they have a chance to compete at scale. I find this last camp to be the most depressing because those entrepreneurs are truly driving innovation but are not reaping the rewards  — think Netscape vs. Microsoft in the early days of the web. The good news is that if you are in camp #2 and you have unfair connections you are going to crush it.

Understand Your Audience

One of the first rules of writing is to “know your audience.” The reason is simple: when you tell a story you must filter your tone and your words to tailor them to your listening audience. To ground this point in your own experience, think about how you talk with guests over the dinner table versus how you talk with your fraternity brother or sorority sister from college. We already tailor our tone or voice — a code word for brand image — when we deal with different people in our lives. In a similar manner, you need to dig deep and define the initial customer whom you wish to serve. For instance, when we were digging up military discounts for TroopSwap we knew that our content and our copy had to appeal to military spouses because that population controls the majority of commerce related decisions in military households. Although it might seem intuitive to market to military spouses for the reasons that I just mentioned it actually took hundreds of interviews for us to realize that we didn’t need to market to our community in a uber-macho military voice but rather in a softer voice with content tailored to military spouses who are 95% female. I literally cringe when I think that we very well could have adopted an aggressive masculine voice when 95% of our alpha customers are females who have not opted into military service save by their decision to marry a service member or veteran. Facebook is a great example of this principle in action. Back in 2004, Mark Zuckerburg wanted to connect people online through their social graph. That seems straightforward enough but where do you start if you are Mark Zuckerburg? Of course we all know that he started with college students before expanding the product to the mass market but that solution is by no means an obvious one or, more importantly, the only right solution. We just don’t have a counterfactual. Similarly, Red Bull started their brand with distribution to high-end clubs and to famous snowboarders — they actually refused distribution from grocery stores and from gas stations in the beginning — until they felt they had sufficiently associated their product with a particular type of lifestyle. These examples illustrate why understanding customers and your company’s strategic vision is so important. Like an author, you need to understand how your novel ends even while you are writing the opening pages of the story.

Find A Mentor

If you are a first-time entrepreneur like me then you absolutely need to find a mentor who has experience in the space you are targeting and a passion for your business. For me, Kelly Perdew is that mentor. A successful entrepreneur several times over in his own right, Kelly has indirectly and directly saved TroopSwap many times over. With investors, he provided much needed credibility because our angels trust him and they know that he will serve as their representative inside the company. With strategic partnerships, he introduced me to key contacts and to great legal counsel that helped us avoid any crippling clauses that would compromise our business. With employees, he was a great sounding board for everything from equity option packages to individual phone calls where he could talk about the business from his perspective as a successful technologist and businessman. He also insisted on background checks and due diligence for employees that helped steer us clear of a few unsavory characters — that could be it’s own blog post. For all intents and purposes, Kelly is a TroopSwap co-founder. We would not be a company today without him. Successful entrepreneurs will have many mentors who are experts in different fields, but, for first-time entrepreneurs, you need to find a single mentor who will connect you to their own network. I cannot emphasize the importance of this section enough. For a first time entrepreneur, finding the right mentor is every bit as important as identifying a big problem.

Find the Right Partner

Michael Jordan had Scottie Pippen. Joe Montana had Jerry Rice. Steve Jobs had Steve Wozniak. At some level it’s enough to say that you need a co-founder or a founding employee whose skills are different from, but perfectly complimentary, to your own. This is easier said that done. Drew Houston, the Co-Founder of Dropbox, wrote an excellent post on Quora about finding a technical co-founder (hint: it’s really hard). The best advice I can give here is to get out to tech mixers and make personal relationships with talented engineers. Co-founding a company together will require more time spent with one another than you spend with your significant other. Most people can figure out who they need to hire but actually getting it done, especially if the entrepreneur is non-technical, is a long hard road unless you have funding. Unfortunately, funding often follows finding the right partner and not the other way around but I am proof that you can land both at the same time because that’s what happened with TroopSwap. 

Be Product Driven

The biggest mistake that I made early on was to allocate money to a marketing budget before we had a minimum viable product. In fact, even after you have a minimum viable product your marketing budget should be minimal as well. My own deck and many other decks that I’ve seen have seed stage funding allocated primarily towards marketing. Now that I’m a little wiser that is a huge red flag that says, “I’m an inexperienced entrepreneur.” In the early days, every resource the company has should be tailored towards developing the best product possible. There should be no marketing spend save for the money necessary to engage customers from your target community in order to iterate your product in a more effective manner. Every entrepreneur should read Steve Blank’s, Four Steps to the Epiphany, before trying to raise money.

The good news is that entrepreneurship is an incredibly rewarding way of life. We are built to create — it’s in our DNA. And what better way to spend your life than to work on products that are capable of transforming the lives of customers in a positive manner. I love being an entrepreneur because I leave everything on the field every day. But there is an incredible amount of responsibility that comes with raising money. I hope that this post shines some light on specific areas that will help you decide whether you are ready to seek financing for your idea.


Blake Hall is the CEO and Co-Founder of, the first ecommerce platform that provides military discounts exclusively to veterans, service members and their families. A combat veteran, Blake led a battalion reconnaissance platoon in Iraq for fifteen months during 2006-07. The Tacoma News Tribune featured his platoon for two weeks after the Army decorated nearly every member of his platoon for valor for heroic actions during a firefight in Mosul, Iraq. His educational degrees include a Bachelor of Science magna cum laude from Vanderbilt University and a Masters of Business Administration from Harvard Business School.

TroopSwap Co-Founder Running Marathon for Homeless Veterans

Matthew Thompson, former Army Ranger and TroopSwap Co-Founder, is running the Honda Los Angeles Marathon tomorrow to raise awareness and funds for homeless veterans. Matt said, “I served on four combat deployments to Iraq and Afghanistan and it breaks my heart to know that veterans are sleeping on the streets they fought to defend, so I’m raising money for an organization that’s doing something to fix the problem.” More information about Matt and the Marathon can be found here.

How to raise capital for your startup

Over the last few weeks, I have mentored fellow graduates of Harvard Business School, local DC based entrepreneurs and a group of very smart high school students at Thomas Jefferson on the nuts and bolts of how to raise capital for their startup. As I talked to my friends and fellow entrepreneurs, I’ve come to realize how little many entrepreneurs know about early stage financing. Over the last ten months, I’ve raised 3.5M for my own startup, TroopSwap, an ecommerce platform focused on veteran and military discounts.  We raised the first million via convertible debt, while the additional 2.5M was raised through equity.

My experience with fundraising has exposed me to the advantages and disadvantages of different types of financial instruments. I’ve also learned about the psychology of raising a round and how to effectively structure a round in order to sustain forward momentum and to ensure that commitments to invest actually materialize in the form of deposits in your company’s checking account. While nothing I’m writing in here is a secret and no one method is more right than another, there are certain norms and best practices that should be followed in order to keep as much of your time free to focus on your business as possible. I certainly wish that there had been a blog post that covered everything I need to know in detail when I was putting together my own round.

In addition, this is my first time building a company, and I certainly did not have experience raising capital before this venture, which brings me to my first point.

Find a Mentor

In order to raise capital, you need to find a mentor who has been successful in the vertical you are entering. Your mentor should have three vital characteristics:

  • Their reputation is impeccable among both investors and business contacts
  • They have a passion for your idea and for you
  • They have held executive level positions in the space you are entering

Your mentor plays an invaluable role when dealing with investors. Beyond giving a first time entrepreneur an invaluable dose of legitimacy (and reassuring investors that a first time entrepreneur won’t blow up his/her startup), your mentor can handle questions regarding the round that will help you avoid awkward or heated conversations with your investors. If the mentor and the entrepreneur divide their responsibilities with respect to financing questions and business questions, then you will have an optimal relationship to raise capital. There are only two rules:

  • The mentor demurs on questions of vision and strategy when dealing with investors except to note that you are a rockstar and the only reason he is spending time with you is because he loves you and the idea.
  • The founder demurs on questions regarding deal terms and the financing and allows the mentor to serve as the single point of contact for all investor questions.

The final thing you need is an investment from your mentor. Inevitably, investors will ask your mentor whether he/she is investing in the round as well. If the answer is no, then that will raise a ton of red flags. It’s also an issue of integrity and aligned incentives. As much as your mentor might claim to love you and the business, cash is truth and the smart money will walk if your mentor isn’t investing in the round.

How much equity should you give up?

A typical VC round is 20 - 30% of your company’s equity.

Convertible Debt vs. Equity

An equity raise is relatively straightforward. The entrepreneur sells a % of his/her company, typically 20 - 30%, for a particular amount of capital. A typical round might look something like this:

  • Pre-Money Valuation of the Company: 8M
  • Size of the Round: 2M
  • Post Money Valuation: 10M (8M Pre Money + Cash Raise of 2M)
  • Investors Stake in Company = 2M/10M = 20%

The trick to putting together a round like the one described above hinges on arriving at an acceptable valuation for your startup. For a startup that may not have revenue, this is no easy task. In that scenario, the entrepreneur and investor might choose to finance the business through convertible debt.

Convertible debt is an instrument particularly suited for pre-revenue startups where an initial valuation would be a number pulled out of thin air. In this scenario, an entrepreneur might decide to offer a convertible note in order to defer the valuation of the company to the next round of financing when a sophisticated investor will be able to place a reasonable valuation on the company. In exchange, the entrepreneur will offer investors interest on the invested capital as well as the right to convert their capital into equity at a discount when the company raises a round at a specific valuation.

For instance, a typical convertible note might have these terms:

  • Size of the Round: 1M
  • Interest Rate: 10%
  • Conversion Discount: 20%
  • Conversion to Equity Trigger: Series A Round of 2M or greater

If an entrepreneur raised a round of equity twelve months later at a Share Price of $25, then the note would convert as follows:

  • Principal + Interest = 1.1M
  • Share Price ($25) * Conversion Discount (.8) = $20 Share Price to Convertible Noteholders
  • Convertible Noteholders Shares = 55,000
  • Series A Investor @ 1M = 40,000

I didn’t note how many shares were outstanding in this hypothetical scenario which would enable you to calculate the percentage of ownership. For example, if there are 1M shares issued and outstanding then the convertible noteholders have 5.5% of the company. If there are 300,000 shares issued and outstanding, then they have 18.3% of the company. The large differential between 5.5% and 18.3% illustrates a deeper debate on the incentives associated with a convertible debt raise.

The large differential in percentage ownership noted above is related to execution. Linking the valuation to a later round of financing allows the entrepreneur to avoid dilution through superior execution; it also allows the convertible noteholders to capture a greater share of the company if the entrepreneur fails to execute well and raises equity at a lower valuation. In theory, the incentives inherent in a note should spur the entrepreneur to work harder to execute and to ensure the company succeeds which creates a winning scenario for everyone, but investors also have an incentive to wait to help the entrepreneur until their convertible note becomes equity.

Depending on market conditions, an entrepreneur might choose to put a cap on the valuation at which the note converts into equity, say 8M, although some rounds go uncapped because the market supports more favorable terms for the entrepreneur or the investor simply wants an option to invest more money in the company during follow-on financings — Yuri Milner and SV Angel’s convertible note investments in ycombinator companies is a good example of this strategy. The most important thing, however, is that your mentor and your board members are investing alongside your investors so that they share the same risk and accept the same terms.

No matter how you choose to raise your capital, through equity or through convertible debt, you will have to negotiate — and that leads to the next question.

When and with Whom Do You Negotiate?

(First, you should remember that you aren’t supposed to handle this conversation, your mentor is the single point of contact) Not all investors are created equal and you shouldn’t treat them as if they are equal. If you are raising 1M with a minimum investment of 25k, then you should resist the temptation to negotiate with investors who are only putting in 25k - 50k. If you begin to make concessions to small investors, then you create a horrible precedent that will encourage your investor to keep asking for more stuff down the line and you open up every piece of the deal to negotiation with all of your other investors. Your mentor will never make this mistake if they are competent.

When dealing with an investor coming in at 25k - 50k who wants to negotiate, simply reply that you are open to changing the terms if they want to put in an investment of 500k or more, otherwise the terms are what they are. This position is a fair one and it will help you avoid needy investors who don’t have much skin in the game but try to armchair quarterback your company from the sidelines. It’s much better for you to hold firm and to only deal with investors who take your company seriously enough to put in a large amount of capital.

How Much Should I Raise?

You should figure out the number you think you need to hit your targets and then roughly double it. Entrepreneurs are overly optimistic, it’s in our DNA. If you think you need 500k then you should try to raise 750k - 1M. When the cash burn is higher than expected (and it will be), the extra capital can make all the difference because it allows the entrepreneur to keep operating the business rather than to go out and waste time raising capital. Your time is much better spent on the business than with investors and you will be happier.

For the legal documents, you should instruct your lawyer to leave the round open up to 2X what you raised. That way, if you need to take on an extra 100k - 200k down the line you will have the flexibility to ask your investors to simply wire it over rather than to re-create an entirely new round. You get to save a lot of time and money because the documents are already on file and the terms of the deal are clear to your investors. Your investors get a bit of a sweetheart deal investing capital on the same terms after a significant amount of time has elapsed and you have (hopefully) increased the value of the company. It’s a win-win.

How Should You Structure Your Round?

If you are raising capital via VC, then you don’t have to worry as much about the mechanics of taking on capital and organizing a round. On aggregate, VCs are moving away from pre-revenue startups, however, and investing capital in growth businesses. Happily, the cost of starting a tech company has fallen dramatically thanks to cloud computing and angel investors have largely stepped in to fill the gap. When you are raising capital via angels, your investors will ask what your “first takedown” or “first close” is for the round and you should be ready with an answer.

The first investor to give you 25k takes a much greater risk than the last investor who puts in 25k to move your round from 975k to 1M when the risk is shared and you already have plenty of capital.

So why would that first investor take more risk and write a check? Exactly.

Without some sort of protection for that first investor, you could go out and spend the capital they invest without raising from anyone else. Most investors don’t want to hear, “I’m sorry. I bought ten MacBook Pros, your 25k is gone. No one else invested.” Since most investors only want to invest if other people think your idea is viable and will open up their network to help you, that scenario is unacceptable. The “First Close” solves this problem.

When structuring the round, the entrepreneur must decide the minimum amount of capital needed to achieve key milestones that would enable the company to achieve organic profitability or to achieve traction that would enable the company to raise more capital at a higher valuation. For a 1M raise, the first close might be 500k. That number will be written into the legal documents for the round. 

The first close binds the entrepreneur to raise 500k before the company is allowed to access the capital or “take down the round.” If the entrepreneur raises 475k but no more than that, then tough luck — the money must be returned to the investors. This legal protection ensures that your first investor who writes you a check is only committed to you insofar as you can convince other investors to invest as well until you have cleared your first close target.

OK, investors agreed to my terms and “are in”, now what?

You should anticipate that 20 - 30% of the money that investors have verbally committed to you will not end up in your company’s bank account. Additionally, investors have an incentive to wait and watch your company perform. The more time elapses before they actually write a check the more time they have to observe you execute and to see if the company risk is going down or up. The way to force the issue and to get a hard yes or no from people is to set a deadline for your first close. (** Give yourself plenty of time! You’ll need at least 2 - 3 months to hit your target.)

Once you’ve set your deadline for your first close, you should set a deadline one week in advance of that date and tell your investors to wire or mail their funds in by COB that day. Even after you and your mentors follow up with your investors, I guarantee you that at least a third of your investors will not wire funds over by the soft deadline. The excuses will cover the spectrum: unexpected business trip, family emergency, need time to free up investments for liquidity.

Even with your mentor helping you to herd your investors, you will find that the remainder of your investors will only wire their funds over at the very last minute when you inform them they are about to miss the deal. Some investors will fade away altogether, so prepare for a first close that is lower than you had anticipated. No round is secure until you have the cash in hand, regardless of the great things you hear from prospective investors at your meetings. Plan accordingly.

Should I always go for the highest valuation?

Simply, no. There are many different reasons that could influence you to choose an investor offering less money (see not all investors are created equally) but just as important are the implications that your valuation will have for future financings. If you raise 5M at a 40M valuation you might feel like a hero, but, if you miss your targets, the market softens and you have to raise again — at a lower valuation — you will lose the majority of your company. Beware Pyrrhic victories.

Anything else?

The first investors you pitch will have a lot of questions. Write them all down and you will find that they are themed around weak points in your pitch and business plan. Those questions will keep your investors from writing checks. They could be related to the size of the market, the team, the business model, distribution, whatever. Once you figure out what is holding investors back from writing a check, you need to get out on the street and talk to customers and recruit talent.

Be tenacious and never take no for an answer. You are only as strong as your will.


Blake Hall is the CEO and Co-Founder of, the first ecommerce platform that provides military discounts exclusively to veterans, service members and their families. A combat veteran, Blake led a battalion reconnaissance platoon in Iraq for fifteen months during 2006-07. The Tacoma News Tribune featured his platoon for two weeks after the Army decorated nearly every member of his platoon for valor for heroic actions during a firefight in Mosul, Iraq. His educational degrees include a Bachelor of Science magna cum laude from Vanderbilt University and a Masters of Business Administration from Harvard Business School.

TroopSwap & Regal Cinemas Partner to Bring Discounted Movie Tickets to the Military

TroopSwap & Regal Cinemas have joined forces to bring discounted movie tickets to military and veteran households across the country. TroopSwap, the first ecommerce platform exclusively for the military, is the first platform to verify the military and veteran affiliation of its user base, allowing the site to partner with premium brands to make a difference through military discounts.

A Selfless Generation

At first glance, retired Sergeant First Class Bob Vandelinde, a veteran of the Korean War, seemed pretty normal, notable for his lucidity after eighty one years, but generally unassuming and affable. A wide smile creased his square jaw often as the former Gold Glove Boxer watched fighters strike each other from our ringside seats at a Spartyka Nation competition in Norfolk, Virginia. He made no reference to his service when we talked, nor did he ask me about my time in Iraq. Like so many of his generation, SFC Vandelinde carries himself with humility. When pressed about the actions that won him the Silver Star sixty-one years ago, he gave me a wry smile and patted me on the shoulder. Not ready to talk about it. I wasn’t going to push him. “You know,” he said. “I didn’t even know where Korea was on the map when they sent us.”

He certainly left his mark while he was there. SFC Vandelinde, along with seven other men, was manning an outpost when he was attacked by a Chinese battalion estimated at two hundred plus men. According to his Silver Star citation, as SFC Vandelinde “moved from protective cover to silence a wounded enemy soldier who was attempting to guide an attack in his direction, he was confronted by a large attacking force estimated at over 200 strong.” SFC Vandelinde successfully silenced the soldier guiding the attack and killed or wounded several more Chinese soldiers while he was alone in front of the lines. Despite being shot, hand grenaded and bayoneted in the face, SFC Vandelinde suppressed the attacking force with hand grenades and rifle fire before returning to protective cover.

At his Silver Star Ceremony, SFC Vandelinde said, “It’s definitely an honor, and a humbling experience. You act, and react to circumstances without thought, or fear. I will accept the Silver Star on behalf of the other seven guys. Without their bravery, and the grace of God, I would not be here today.”

On the 14th of August, SFC Vandelinde keynoted a tandem skydiving Wounded Warrior event organized by Skydive Suffolk and TroopSwap. Over $15,000 dollars were raised for Wounded Warriors. Bob, at age 81, jumped from a perfectly good airplane at 13,500 feet to help others. After watching him land on the dropzone, I reflected that if you can fight a Chinese battalion by yourself and jump out of an airplane then there probably isn’t much in the world left to fear. But, as SFC Vandelinde unhooked his harness, his son confessed to me that he was terrified.

SFC Vandelinde, you see, hadn’t told his wife the real purpose of his trip. And now he had to tell her what he’d done. To listen to his sons, the conversation would be a rough one. Unfortunately, they don’t give Silver Stars for those battles.

TroopSwap, Red Bull Air Force and Wounded Wear Team Up for Wounded Warrior Skydiving Event

The second annual Jumping for a Purpose will take place at Skydive Suffolk over Memorial Day weekend, May 26th and 27th, from 9 AM until 6 PM. After raising $17,000 dollars for Wounded Warriors during last year’s event, organizers from and Wounded Wear coordinated with the United States Navy and the Red Bull Air Force, Red Bull’s official skydiving team, to augment the event with a flyover from a fighter jet and a professional aerial performance.

In keeping with last year’s tradition, TroopSwap and Wounded Wear expect to have a Wounded Warrior from every conflict dating back through at least Vietnam present to participate. Walter Reed is also sending Wounded Warriors to participate in the event. After last year’s event surpassed expectations by attracting over 3,000 attendees on a single Saturday, leaders from TroopSwap and Wounded Wear estimate that over 5,000 attendees will participate in the upcoming celebration of the unbreakable will  and spirit of America’s finest men and women.

Sponsors are needed to offset the cost of jumping each of the Wounded Warriors participating in the event. Supporters may request more information by e-mailing or by donating directly through Wounded Wear’s website:

Your donation will support an amazing experience for a Wounded Warrior like Lance Corporal David Collins:

About TroopSwap: is the first e-commerce platform for military discounts exclusively for military families. Our mission is to reward a life of service. We limit eligibility to veterans, service members, and their immediate family members. We partner with merchants to provide great deals for the military community. We only employ military spouses in the markets where we are active. 10% of our profits are donated to the Wounded Warrior Project. To learn more, please e-mail: aaron(at)troopswap(dot)com, follow us on Twitter @troopswap or like TroopSwap on Facebook at

Why Your Company Should Hire Veterans

The fundamental challenge for any organization is to take a group of individuals and to re-form their identity so that each individual works together as part of a cohesive group striving towards a common purpose. By definition then, an individual must subordinate selfish tendencies in order to allow the group to operate most efficiently. For instance, the CFO probably shouldn’t be mopping the bathrooms if the company is to develop proper budgets or to have the proper advice while negotiating contracts. At the other end of the spectrum, the CFO should ensure his own actions are aligned with the best interests of the company, shareholders and employees. While many companies have proven adept at building strong cultures capable of positively transforming individuals’ self-identities at all levels, few organizations are as skilled as the United States Military at re-forming an individual’s sense of self-worth. As a result, veterans are excellent additions to any organization because their sense of self-worth is tied to the well-being of the group, they have learned positive habits and they have been given greater leadership responsibilities relative to the vast majority of their peers.

The purpose of basic training is to take an individual and to re-form their identity around the concept of a Soldier, a Marine, a Sailor or an Airman. All actions fall into one of two classes: behavior that benefits the group or behavior that harms the group. Showing up late for a formation is an example of a behavior that harms the group as the group is less effective without each member of the team. As a result, a drill sergeant might spend several hours reinforcing the importance of being on time for formation by making the group suffer through a prolonged episode of physical exercise. Interestingly, the punishment meted out almost always affects the group, rather than just the individual at fault, for the drill sergeant continually attempts to teach the group that the deviant actions of one person will affect many others who depend on him to do his job in a war zone. In fact, the drill sergeant may even require the offender to watch his peers suffer, while forcing him not to participate in the group punishment, in order to reinforce to him the selfish nature of his actions. And, because the guy who showed up late will get an earful from his peers, an individual will face tremendous peer pressure to avoid deviant behavior — a powerful feature of the military’s culture that leads to the formation of positive habits over time.

For positive behavior, the military encourages individuals to develop their unique attributes that further the well-being of the group. Badges and awards are given out for excellence performing tasks that positively affect the group. A Marine who spontaneously takes charge of a situation to treat a sucking chest wound during a training exercise might receive an achievement award and public recognition for his actions in front of the group. Taken to the extreme, a Soldier who sacrifices his life for other members of the group is revered and treated as a hero.That story then becomes a larger part of the military mythology that reinforces positive behavior.

The military functions so effectively because the cultural pressures that reward positive behavior and punish deviant behavior become more powerful, not less powerful, the further an individual progresses in his military career. As an individuals’ social network becomes increasingly intertwined with other members of the military, the consequences for deviant behavior affect an individual in a more powerful way while the accolades given for positive achievement are likewise amplified. Thus, the military creates a powerful environment that trains an individual to evaluate and validate his actions, and by extension his sense of self-worth, by examining their impact on the group. The military has created a powerful indoctrination system that incubates and develops positive habits, and, since the best predictor of future behavior is past behavior, veterans are more likely to take those behaviors with them into the workplace.

Finally, veterans have been given far more leadership responsibility at a far earlier age relative to the vast majority of their peers. From the 22 year old Infantry Platoon Leader charged with making life or death decisions in combat for up to 46 men to a 30 year old Sergeant First Class managing hundreds of millions of dollars of equipment, the military entrusts more responsibility to people at an earlier age precisely because the culture of the military continually pushes people to develop themselves, to find answers in ambiguous environments and to accomplish the mission regardless of the challenge because a veteran’s self-identity and self-worth rides on his success to perform his mission to standard.

The military’s unique ability to instill positive habits in its’ workforce makes it fertile recruiting ground for corporate recruiters. A well organized business training program can teach the fundamentals of the business model to new hires but it cannot teach those new hires to internalize the values and goals of the organization to the extent that a veteran will grasp those intangible elements. How much would it cost to train someone to develop habits that put the well-being of the group ahead of their own self-interests? Is that even possible outside of a military style indoctrination process like basic training?

The business world looks to the military for lessons on leadership, so it makes sense that the business world should also look to hire veterans to enhance their workforce. Because veterans are influential by virtue of their exceptional experiences, they will coach and mentor their peers to improve the organizational culture in many subtle ways that may not be immediately visible but might make the difference in a critical situation. Plus, you might not need to hire a security guard.


Blake Hall is the CEO and Co-Founder of, the first ecommerce platform that provides military discounts exclusively to veterans, service members and their families. A combat veteran, Blake led a battalion reconnaissance platoon in Iraq for fifteen months during 2006-07. The Tacoma News Tribune featured his platoon for two weeks after the Army decorated nearly every member of his platoon for valor for heroic actions during a firefight in Mosul, Iraq. His educational degrees include a Bachelor of Science magna cum laude from Vanderbilt University and a Masters of Business Administration from Harvard Business School.

What Does It Take to Build A Successful Company?

The twisting road of entrepreneurship can lead to some interesting encounters. Last week, I was fortunate enough to meet Steve Case, the Founder of AOL, Michael Dell, the CEO of Dell Computers and Dan’l Lewin, a senior executive at Microsoft and a Silicon Valley legend. Those meetings came after I had a conversation with Andy Rachleff, the Founder of Benchmark Capital, about the characteristics of successful CEOs.

The most powerful characteristic I recognized in each of the executives I met was the passion and the will they had to make their business succeed. But what are the underlying personality traits that lead to success? Entrepreneurship is ultimately the art of making people believe in what you are doing: from your first employees who leave their secure jobs to take a chance to your first customers who take a risk by spending their money with an unknown brand. Certainly, the last two years have taken their toll on my body and rubbing elbows with CEOs is a luxury, not a necessity, amidst many other time sensitive issues that demand my attention, but sometimes it’s nice to step back and listen to leaders who have built their businesses the hard way. The lessons learned aren’t necessarily intuitive.

For instance, Andy Rachleff asked me, “How many really successful CEOs can you think of who are “nice guys”?” I wasn’t able to name one on the spot and I’m not sure what to make of that observation.


Blake Hall is the CEO and Co-Founder of, the first ecommerce platform that provides military discounts exclusively to veterans, service members and their families. A combat veteran, Blake led a battalion reconnaissance platoon in Iraq for fifteen months during 2006-07. The Tacoma News Tribune featured his platoon for two weeks after the Army decorated nearly every member of his platoon for valor for heroic actions during a firefight in Mosul, Iraq. His educational degrees include a Bachelor of Science magna cum laude from Vanderbilt University and a Masters of Business Administration from Harvard Business School.