How to Win a Startup Pitch Competition

Article Provided by Trey Bowles, CEO and Co-Founder of The DEC.



Win or lose, startup pitch competitions represent a great opportunity for your business to generate buzz, connect with potential mentors and advisors, and even begin the process of securing investors. Pitch competitions can also help you to sharpen and hone your mission, strategy and other key components of your business model. Entrepreneurs would be well advised to approach pitch competitions with these “fringe benefits” in mind.

That said, winning a pitch competition could provide you and your team with a sense of instant validation. Competition is a defining feature of the startup landscape, and you’ll need to exploit whatever advantages you can in order for your business to thrive. Keep these tips in mind as you prepare to enter the fray.

Play the game the right way.

What is the format of the competition? How much time will you be allotted? Is your presentation reliant on a single spokesperson, or can it be more free flowing and allow for the articulation of multiple points-of-view? How will the Q&A be handled? On what criteria will the judges be scoring your presentation?

First, make sure you address the main points that are listed on the judges’ scorecard so you can check the boxes on that sheet and then cover the other important areas you want to communicate to the judges. For example, if the judges are grading you on information about your “team” and you don’t talk about your team at all during a pitch, how can they give you anything but a low score? Do you shoot yourself in the foot by not playing the game by their rules?

Make your preparations specific to the competition at hand. Don’t deviate from what’s expected of competitors. Certainly don’t attempt to wrest control of the process from the moderator or judges, or try to slip in content that hasn’t been requested. What’s true of successful test-taking applies: Follow directions, show your work where applicable and don’t try to bend (or break) the rules.

Think outside the PowerPoint box.

We all know brevity is essential to any pitch. PowerPoint is one of those tools that can truly enhance a presentation. Expert users know how to leverage PowerPoint to effectively convey information that doesn’t transmit (or stick) well orally. But how many times have you sat through a presentation in which the speaker simply repeats the information on their PowerPoint slides? Is this really an efficient, or particularly exciting, use of anyone’s time?

Less is more. If your audience is too busy reading the 17 lines of copy on each slide, you’ll distract them from actually listening to the key part of your presentation (that would be you!). If there must be a graphic component to your pitch, be creative with that aspect of the presentation. Remember that PowerPoint slides are visual and, as such, can make an emotional appeal. What if your PowerPoint dispensed with charts, figures and language altogether and instead used simple graphic elements to suggest, illustrate, persuade and inspire? Can you really make an effective argument about how innovative you are if you are trotting out the same kind of presentation these judges have seen time and again.

Consider “the TED talk” model here, and think about the ways in which all five senses, not just the visual, present opportunities to make an impression.

When it comes to defense, don’t be defensive.

In the course of your presentation, you may feel yourself being grilled by the judges. You may even receive some negative feedback. Don’t get rattled, don’t try and dodge the difficult questions and don’t push back (or push back only very gently, focusing on the facts and not your impressions of what you may have just heard). Yes, you want to show you believe in your idea and that you’re committed to it in the face of naysaying. But you also don’t want to portray yourself as inflexible, disingenuous, argumentative or petulant.

Use the Q&A time you have with the judges in a creative way. Yes, answer the questions they ask but make sure you also use that time to communicate information you didn’t get to fully cover in your presentation. Use the standard public relations mentality of ATM: Answer, Transition, Message. Answer the question they ask, transition back to something you want to talk about and then stick the message of your presentation. For example, if a judge asks you whether your technology is scalable, you answer “yes” or “we think so” followed by specifics: “but what we think is an important component of what we’ve seen is having already signed up 100,000 users, and with these three strategic partnerships will add another 500,000, allowing us to prove and showcase the scalability of our product.”

Side tip: Remember the last slide of your presentation is likely going to be up on the screen during the entire Q&A time. Put information on the final slide you believe to be most vital to communicating your company’s offering. If you have the CEOs of Netflix and Apple on your board, leave your team slide as the last slide. If you’re generating substantial revenue and cash flow, show your traction. Too often, we simply put “thank you” or our contact information on the last slide. Don’t squander that space! You need to control the pitch process and make sure you play by the rules, but also give yourself the ability to accomplish your goal of communicating your company to the judges

Accept any criticism offered, even if it isn’t constructive. Besides, it could be that the judges are simply testing your resolve and ability to remain focused. Go with their flow, as it were, while not allowing yourself to become distracted.

Remember that pitching is a performance. In your preparations, rehearse with your team and do some exercises to hone your improvisational skills. Put yourself in the position of a potential judge or have another team member take on that role and grill you on those questions you least anticipate being asked during your presentation’s offensive. Imagine the worst-case scenario for your pitch and see whether, in rehearsal, you can’t overcome or work around it.

Emphasize the “who.”

Of course, the “what” of your business is crucial. You want to make sure anyone walking away from your presentation does so with a firm sense of what your business actually does: the problem you’ll be solving, the essential service you’ll be offering, the unique benefit your customers will enjoy. But remember that you don’t have a monopoly on these aspects of your business model. Assume there are multiple startups out there aiming for exactly the same markets. What differentiates your company from these competitors?

Think of your company’s self in broad terms. “You” are a part of a larger group of mentors, advisors, co-founders and board of directors. The talent you’ve assembled and the “big names” you may have lined up as consultants and angel investors are all an essential part of the “who” of your organization. You can often create more interest, excitement and intrigue around your company if you highlight your team, your mentors, your strategic partners or investors. “You” are here to tell the story of your business. “You” need to communicate the passions that drive your team, the accomplishments to which you can already point, your willingness to be objective and be honest about your strengths and weaknesses and your ability to best represent yourself.

Being personable and charming is never a bad thing. However, these competitions are not popularity contests. Judges are gauging your competence as well as your credibility, and your confidence—how comfortable you are in your professional skin—is an index of that competence.

Give them something to remember you by.

Put yourself in the position of a competition judge for a moment. You’ve just sat through nearly 100 rapid-fire pitches. No matter how extensive your notes, you’re simply not going to remember every single critical detail about what you’ve just seen and heard. Your job as a presenter is to end your presentation with what long-practiced pitchers call a “memory cue.” Is there an anecdote, a joke, a gesture, even a catchphrase that can be the one thing the judges remember about your presentation?

These things may seem inconsequential, but memory does work by association. The simple fact that you relied upon a pithy metaphor to describe how your business will transform the industry could be the difference between your pitch fading into the background and the judges remembering your business’ future potential at all. And don’t be afraid to be literal here. Conclude your presentation with a call to action in which you tell—or better, show—your audience precisely what you want them to remember.

These five ways to tailor your business pitch for the competitive circuit are a proven model that I’ve seen many great entrepreneurs use in the course of my career. In the end, it’s important to learn from your mistakes and learn from those who have gone before you to make sure you put your best foot forward, regardless of your pitch’s audience.

For more information on how to put together knockout pitches, please visit our events page for information on programs, classes and events where you can get direct feedback on how to improve your pitch.

Five Ways to Perfect Your Business Pitch

Trey is the founder of the Dallas Entrepreneurship Center, check out their efforts at twitter handles @theDECtx and @treybowles.


Pitching your business is equal parts art and science. Yes, you do have to be able to marshal and command facts and figures. More than that, however, you have to able to inspire and motivate individuals by virtue not just of your ideas, but your personality. Before you enter that boardroom (or elevator) with PowerPoint and agreements at the ready, review these tips for preparing your pitch for success.

No. 1 Start strong.
You need to catch and retain the attention of your audience. An “attention getter” can be a game-changer for a presentation. If you don’t engage your audience in the first 30 seconds you may have lost out on the chance for your pitch hit home. But there’s no one-size-fits-all attention getter. You have to determine the best way to interact and connect with the particular audience to which you are pitching, whether it’s investors, consumers, potential partners or judges in a pitch competition.

A piece of advice: If you’re pitching in a competition, please, for the sake of all that is holy, pitch the things the judges tell you they believe are important, or use the scorecard they are judging off of as a guide. If one of the marks on the scorecard is “Team,” yet you didn’t communicate anything about your team, they can’t give you credit for that point.

No. 2 Be able to defend your assumptions.
I frequently tell entrepreneurs these two things: 1) You need to have assumptions for your presentation and your financial plan, and 2) you must be able to defend your assumptions. I know a lot of the time you don’t have all the answers for how quickly you’re going to grow or what the acquisition cost of a customer might be, BUT your audience might not know that either. You can find a lot through market research and qualitative and quantitative analysis. I also think deductive reasoning helps explain why you believe what you believe.

In raising money, there are several ways to go after it. Sometimes it’s just being the best salesperson (I have seen money raised for completely unrealistic ideas because of good salesmanship). For me, in all of the money I’ve raised in my career, it came from a firm grasp and understanding of my company, its financials and the ability to defend my assumptions. For example, if you show in your financials that you’re going to hire a salesperson in June, don’t say they’re going to be at full sales capacity in the first month. Oftentimes it takes a few months to get up to speed. On the flip side, don’t show hockey stick-type growth without an explanation of what you did to achieve that growth. (By the way, if you put hockey stick growth into your financial statements, this just ensures I’m going to throw them away.) You can’t predict hockey stick growth, and if you think you can, then it shows how little you know about your company.

Costs are different. You should have pretty clear understanding on what your costs/expenses might be. Those questions can be answered with a phone call or some simple research. But because those are all very discoverable, make sure to not mis-forecast them. If you can’t be bothered to get the easy answers correct, how can we expect you to nail the other things necessary for your success?

In the end, you’re really making your best educated guess. One of my greatest friends Jason Illian always says, “The only thing you know about your financials is that they’re wrong.” They may be too high or too low, but you must use this opportunity to showcase to your audience that you have realistically thought through what the future of your company will look like.

No. 3 Answer questions before they are asked.
In a typical pitch, we’re already aware of what the audience wants to know. They really want to know a few main things:

First, they want to know what your company does and get a clear understanding of your product or service. You’d be surprised how many times I leave a pitch asking myself, “What was it that company did?” This nugget can often be shared at the conclusion of the attention grabber. Next we want to be convinced that there’s a market or demand for your product or service. If you can’t show the audience there’s a clear and viable market for what your company has to offer, there’s no reason to continue the conversation. Often this includes a competitive analysis that demonstrates where your product or service fits in. Next, and maybe most importantly, we want to know what makes your product or service DIFFERENT. What is your core differentiator that will make your company succeed? Then we need to know the sales and marketing strategy for your product or service. If you’ve convinced your audience there is a market, we now need to know the channels for distribution, how you’re going to market and your sales strategy for success. We then want to understand who your team is and why you’re the right team to make this company work. And lastly, we want to understand your financials or how you’re going to make money and how much you plan to make. Don’t come in with unrealistic numbers, like you’re going to make $41 million in your first six months. On the other hand, if you show you’re going to make $32,000 in profit after three years, that’s probably not the type of return that’s going to embolden an investor or partner to support your venture.

Answer these questions before you get to the Q&A so you can use that time for other things. If you can demonstrate you have a grasp on these key points and that you’ve built everything upon realistic assumptions, then you’ve already shown you should be in that room and have a command of your business and where you’d like it to go.

No. 4 Use your Q&A time wisely.
You’re typically given a certain amount of time present your pitch. In a competition, that can be anywhere from one to 10 minutes, and in an investor meeting, maybe 15 to 30 minutes. Make sure you use the question and answer time to cover the content you believe to be important but that you didn’t have time to address in the main pitch presentation. It can include giving more information about your team, further explaining your technology or product/service. It could also be a great time to expound upon anything you don’t think “landed” in the presentation. Make sure to use your entire time and not just the allotted time that was put into your presentation time. Another helpful hint: I like to make the last slide of my presentation the most important slide. Often this would be a team slide.

No. 5 Team, team, team.
I always tell people there are three things investors look for before making an investment: 1) concept, 2) team and 3) ability to execute. All of these relate to the idea of team. Whether you’re a first-time entrepreneur or a repeat offender, it’s important to recognize the importance of the people you’ve assembled around you. When hedge fund managers make bets on companies, it’s only after much due diligence with the management team. It’s no different for entrepreneurs. You need to have the best team you can to help you succeed.

Here are a few things to consider in that regard. First, a team is not restricted to the co-founders or the first set of employees. A team includes your mentors, advisors and board of directors. As such, you want to put together the best comprehensive team you can, not unlike how you would assemble players for a basketball team. You always want your best five players on the court—it would be ludicrous to have Lebron on the bench in a clutch situation, right? If you can convince an investor you have a great team, it’s far more likely they’ll invest and far more likely you’ll have accurate assumptions for your financial plan, which strengthens your pitch. This process starts and ends with team, so if you’re not willing to spend time and effort to put together the right group to launch your business, then you’re starting at a disadvantage.

These five ways to perfect your business pitch are a proven model that I’ve seen many great entrepreneurs use in the course of my career. In the end, it’s important to learn from your mistakes and learn from those who have gone before you to make sure you put your best foot forward, regardless of your pitch’s audience.

My Perspective On What The Techstars Acquisition of UP Global Means for Startups

Throughout our ecosystem and through our own entrepreneur centers, we often look at and evaluate better ways to usher companies along the life cycle of entrepreneurship. There is a journey that as an entrepreneur, you embark upon that starts with an idea and can take off from there. Our goal is to provide resources, tools, connections, capital, promotion, and overall empowerment to entrepreneurs. But we can only fill so many gaps, and provide certain necessary elements that an entrepreneur needs along this journey.

As we identify entrepreneurial support organizations that exist along the current lifecycle of an entrepreneur, we often look at tools and resources that support an organization from “idea to exit.” Some of the great programs that exist to support early stage entrepreneurs have lived under the UP Global brand. Programs such as Startup Weekend, which provides a jump-start to an idea and a first step into the world of entrepreneurship, and mentor-based program Startup Next which focuses on preparing teams for accelerators or raising seed funding. Key collaborative programs like Startup Digest that connect community members through events and reading lists as well as  Startup Week that bring an entire community together to support the growing activity of different ecosystems across the country.

But, after these programs, where does a company go after it is developing customers, starting to launch its product/service, creating revenue for the first time, or seeking additional capital or instruction to get your business to the next level?

Now enter organizations like accelerators, incubators, coworking spaces, educational programs, etc. One of the great leaders in this space has been Techstars. Techstars and other funding sources offer the necessary capital, networks, and mentorship platforms for companies to move their business to the next level in that life cycle. These organizations step in and help give organizations a leg up on how to effectively grow their enterprise and by combining the elements of capital, connections, and community, they can give early stage entrepreneurs the formula necessary for that next stage of success.

This is why I think the announcement of Techstars and UP Global joining together illustrates a coming together of different key elements of the entrepreneurial lifecycle. Partnerships like this are one critical component of what the future of entrepreneurial support will look like for entrepreneurs. We need to find groups that compliment each other well to enable early stage entrepreneurs through the stages of growing a business. We need to find groups that share similar missions and alignment of vision to ensure that we are appropriately escorting these young businesses through different business stages and providing a pathway to success.

I am encouraged by this announcement and believe we will see huge dividends for entrepreneurs that exist all along this spectrum. I think that by combining the international community of UP Global’s “nodes” or connectors who have a true volunteer spirit to support their local community along with Techstars proven track record for helping companies create long term and sustainable growth, we will be able to see the type of connectivity that will continue to make entrepreneurship more attractive, attainable and compelling to aspiring entrepreneurs all over the world.

Now, all we need is more venture capitalists, private equity, and commercial banks coming along to support the stage beyond where the new future of Techstars and UP Global provides value.