An Investor’s Guide to a Persuasive, Winning Pitch 

Posted by: Leura Craig

Posted on 04/21/2021

An Investor’s Guide to a Persuasive, Winning Pitch 

A pitch deck is a critical communications tool for all startups—it is how you tell the story of your venture, make your introductions to investors, and more. However, it doesn’t take much Googling to see that everybody’s got their own opinion of the right and wrong ways to put together a deck or how to present yourself to investors. In my experience as an investor and former founder, the most successful pitches all boil down to one major imperative: a compelling narrative arc.

When you’re speaking to a person you want to partner or work with, it’s always in your best interest to figure out the most impactful way to sell yourself, your idea, or your business to that particular person or group of people. Effective communication is all about presenting a compelling narrative, and when you’ve only got a few slides and a handful of minutes to share your startup’s story, you have to make every word count.

As with all persuasive writing, who you’re pitching to should inform your tone and diction in each iteration of your verbal pitch and every share of your deck. So, first and foremost, do some digging online to see if you can find any clues about what the investor is looking for in a pitch. It’s entirely possible that they have provided a quote for an article about what they think makes a great deck or that they’ve listed their expectations on their website. Use whatever information you can find to tailor your presentation to their most desired style of delivery without sacrificing your authenticity or personal style. It can be a tall order, but it’s worth the effort.

As more startups have learned about our upcoming pitch event, OutPitch 2021, we’ve received many questions about what we look for in a pitch deck. We really appreciate these questions because it shows that the founders not only want to understand us as investors but also recognize the importance of tailoring their message—a skill that is a boon to the long-term success of any entrepreneur and their company.

If you’ve read this far and you’re a founder interested in pitching to the Outlander team, I’ve got some good news! We’ve distilled the core features of a winning pitch, and we’re more than happy to share that information with you. Ideally, your pitch hits the ten critical highlights below in ten slides or less, leaving your audience with a well-rounded view of you, the founder, as well as the problem you’re trying to solve.

Core features of a winning pitch:

  1. The “why?” or big picture: What is your venture’s overarching vision or mission?
  2. The problem: What is the problem your venture is poised to solve?
  3. The solution: What is your proposed solution to #2? More specifically, how does your venture fit into the solution of the problem you’ve articulated?
  4. The timing: Why is now the right time for your venture’s solution? For example, what is the total available market demand for your product or service?
  5. The founding team: How does your founding team fit into the context of your answers to #2-4? How are your founding team’s backgrounds, passions, etc. uniquely suited to build this solution?
  6. Traction to date: What are your venture’s milestones or traction to date? If you have customer stories, tell them here!
  7. The future: What do you predict your venture’s business model will be once you’re further along? If you are unsure, make a few predictions of what it could be.
  8. The obstacles: What does the competitive landscape look like?
  9. The plan: What is your projected timeline to success? Include any financial projections or major milestones with estimated timelines here.
  10. The ask: How much are you aiming to raise? What milestones do you achieve with the capital? How will you use the capital?

The narrative arc of a winning pitch is as follows: Start with the big picture. Then delve into the specifics and how your founding team fits in. Next, bring us up to speed on your progress thus far, then sell us on your venture’s vision for the future. In your vision for the future, be sure to demonstrate your area expertise by identifying any potential competitors or obstacles, followed by your plans to navigate around them. Conclude with your ask. And don’t forget to tailor the details to your audience!

Test your winning pitch at OutPitch 2021

Now you’ve got a pitch with a compelling narrative tailored to Outlander VC, and we want to see it!

Here’s what you need to know about OutPitch 2021:

Outlander is inviting the most innovative early-stage tech startups in the Southeastern United States to out-vision, outsmart, and outpitch the competition at OutPitch 2021! The live pitch competition winner will receive a $100,000 investment from Outlander VC on a $1M capped convertible promissory note! Read all of the Outpitch 2021 terms and conditions here.

Who can apply?

If you’re the founder of an innovative early-stage tech startup headquartered in the Southeast, you are strongly encouraged to apply! The application deadline is 11:59 pm EDT on May 2nd, 2021.

How long is the application?

The application request form is simple. Just send us your name, contact information, and the name of your startup.

Then, look out for an e-mail from with the link to the full OutPitch 2021 application.

The full application consists of 14 questions, covering your contact information, co-founders, company description, location, product category, website, and pitch deck, and previous funding information

I applied! Now what?

Yay! We can’t wait to review your OutPitch application. Next, our partners will select the top six startups to pitch live to our top-tier venture capital investors and judges on May 18, 2021.

Applications are due in…

Best of luck!

Leura Craig

Senior Partner, Outlander VC

Leura is a former founder and experienced investor who previously bootstrapped two startups as the founding CEO.


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