5 Successful Dealmakers Share Their Top Tips on Raising Capital

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5 Successful Dealmakers Share Their Top Tips on Raising Capital
Image credit: Mary Delaney | The Oracles

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Bootstrapping will only take your startup so far. Many businesses underestimate how much money they really need to keep going and growing, and they run out of runway.

When raising funds, these investor-entrepreneurs and members of The Oracles share their best secrets, tips, and strategies.

Tim Draper
Image Credit: The Oracles

1. Soul-search.

For me, it's all about enthusiasm. You need to show why you need to spend the rest of your life achieving this mission. The mission itself has to be large enough for a venture investment and crazy enough to make a significant impact. The technology must also be unique.

Before you ask anyone for money, make sure this is what you want to do—even if you never get the money. I often ask entrepreneurs this question: "Why? Why are you doing this?" If the answer doesn't burst out of their chest, I'm out. If it does, I lean in. Every entrepreneur should ask themselves this question. Do some real soul-searching before embarking on a life-changing and potentially world-changing venture. Tim Draper, legendary VC, founder of Draper Associates and DFJ

Tai Lopez
Image Credit: The Oracles

2. Test your idea.

I've always used more of my own money and limited outside investors.

Never underestimate trying to raise funds from your existing customers. The modern world of Kickstarter, Indiegogo, and the internet enable you to pre-sell things before they're produced. This has a two-fold benefit. One, it's the same as raising capital, but you don't have to give away equity or decision-making control. And two, it validates whether the idea is good or not—and ensures you're not raising a bunch of money for a business that's doomed to fail.

There was a guy at my house who raised a million dollars to build an app. The second he explained the concept to me, I said, "This is the dumbest app idea. No one's ever going to buy it." And sure enough, he lost a million dollars. Had he tried to pre-sell the app idea, one or two things would have happened. One, it would have sold, and he'd have pre-order sales to fund the business. Or two, he would have gotten the signal that it's a horrible idea that no one will pay for. Tai Lopez, investor and advisor to many multimillion-dollar businesses, who has built an eight-figure online empire; connect with Tai on Facebook or Snapchat

John Hanna
Image Credit: The Oracles

3. Be the unicorn.

First off, before you can pitch your business, someone must be interested in listening. So, create a “30-second elevator sell” to capture someone's attention. Remember: you’re just another business asking for money; there are thousands of you out there.

Once someone is willing to listen, the most important factor is a rock-solid business plan containing the most detailed SWOT (strengths, weaknesses, opportunities, threats) analysis of your business and industry. Ensure that your plan is believable and realistic with enough evidence to substantiate your cash-flow projections: if it's exaggerated—showing a higher than normal profit—you’ll instantly lose credibility.

More than anything else, your investors aren’t just investing in your business (or product), they're investing in you. You’re there to sell "why" they should risk their money in your business, which is no easy task.

Therefore, your certainty will be a key determinant of whether they proceed. Your passion should be so real that your venture capitalists can see and feel the future success. Remember: sales is nothing more than the transference of feelings. Those who have more certainty usually get what they want. If your "Why" is big enough, the "Hows" take care of themselves. John Hanna, author of "Way of the Wealthy" and CEO of Fairchild Group

Roy McDonald
Image Credit: The Oracles

4. Be confident, concise, and clear.

When raising capital, my experience is that banks are the last resort. I prefer joint ventures, equity participation, and loans with profit share.

The most important aspect is to always look from the investor’s point of view and what’s in it for them. Align your business with their purpose to ignite their passion.

When presenting to investors, be confident, concise, and clear about your outcome. You must have a step-by-step plan of what you are offering and how it will work and be monetized. Show investors how they'll make money and have their capital returned.

Investors will ask many questions. You must have clear, well-reasoned answers to their concerns. Offer an escape hatch—a way out—if everything fails.

The most important part is to demonstrate you have a team to produce the intended outcome. This includes the three most important aspects of your operation: marketing, finance, and administration, with monthly/quarterly reports to the investors.

Lastly, always underestimate the profit and overestimate the time it will take. That way, you'll exceed expectations. Roy McDonald, founder and CEO of OneLife

Ken Lebovic
Image Credit: The Oracles

5. Get the details right.

The terms you agree on will be just as valuable, if not more valuable, than the deal itself.

As the largest volume buyer of distressed homes in Illinois, I've seen many real-estate investors come and go. Often, they fund a deal using outside capital, only to realize the terms don't give enough share of the pie to make it worthwhile.

So, don’t be a deal junkie. Only do deals that have enough upside to make your time spent and your investor’s return worthwhile. Time is money. Make sure you get paid accordingly. Once you’ve done several good deals and have shown your investors that you do what you say, consider talking about structuring the next investment opportunity differently.

This is easiest when multiple investors have had a positive experience with you. A good experience always makes it easier for them to say, "Yes!" Over time, your investors will get more comfortable with you; they won't hesitate for smaller returns, knowing their risk is minimal. Ken Lebovic, president of North Shore Holdings; built a real estate empire acquiring thousands of properties over 20 years with no equity partners

Want to share your insights like those above in a future column? If you’re an experienced entrepreneur, please get in touch here.

Want to suggest a future topic for these entrepreneurs to answer? Email suggestion@theoracles.com and it’s very possible we’ll make your suggestion the focus of a future article!

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