Asking for money for your business is always time-consuming, often fruitless, and inevitably stressful. But there are ways to make the process more productive and maybe even a little bit enjoyable--beginning with how, and to whom, you make your pitch. To start, "keep it short," advises Barry Schuler, the former America Online CEO and chairman turned high-profile venture capitalist at DFJ Growth.

He's one of several top investors Inc. recently asked to share their pitching advice for entrepreneurs--based on their experiences vetting thousands of founder pitches, managing billions of dollars, and backing companies including Tesla, Uber, and Twitter. So while there's no one right way to make the money ask, you can get ahead of the game by consulting these investors' secrets for making successful pitches

The Biotech Backer

Josh Makower is a general partner on the health care team of venture giant New Enterprise Associates, which raised $3.3 billion for its most recent fund. Makower, who holds an MD, also co-founded Stanford's biodesign innovation program.

If your pitch isn't going well, it's totally appropriate to say, "Are you with me? Does this make sense to you?" Then you have an opportunity to address whatever the concern is. Spend the time and get to the bottom of it. The worst thing you can do is press on.

If you are on slide one and everyone nods, and there are other bullet points on that slide, move on. Otherwise, if they've already nodded and you're still talking about that same thing, they're going to be checking their email.

The Early Fintech Funder

Amy Nauiokas is founder and CEO of Anthemis, where she invests in early-stage tech companies in media and financial services. Her portfolio includes Betterment and Simple.

Don't be afraid to talk about what keeps you up at night or share your weaknesses. Failing to acknowledge the skills you lack as a founder is the greater weakness.

Ask real questions about the type of relationship investors expect to have with their portfolio companies. 

The Socially Conscious Tech Funder

Jenny Abramson is the founder and managing director of Rethink Impact, a venture fund focused on gender-diverse teams, technology, and social impact. Her portfolio com­panies include Guild, EverFi, and Werk.

Every leader tells us about their own background, but you should also talk about your team. That shows us you're humble and have respect for the other people involved.

Don't be overly conservative about how big the business can get. VCs will require a haircut on whatever numbers entrepreneurs give them.

The Growth Leader

Barry Schuler is managing director at DFJ Growth, one of the first venture firms to focus on growth as a specific practice and an investor in Twitter and Tesla. Schuler sits on the boards of Coinbase, Formlabs, and Giphy.

You can't keep trade secrets from your investors.

The number-one sign of complete transparency is an entrepreneur who says, "I don't know the answer to that question, but I will get it to you."

Keep it short--four bullet points per slide. It really detracts from the pitch if you're up there talking with passion next to a slide that's unintelligible.

The Social Environmentalist

Victoria Fram is co-founder and managing director of VilCap Investments. VilCap makes seed-stage bets on companies that address social and environmental challenges, such as Landit, Neighborly, and Rimidi Diabetes.

Practice answering questions you have the biggest insecurities with, either because of your business model or your ability to present it. You don't need to eliminate all risks or uncertainties, but you do need to know how to talk about them.

Sweat the financial details. You need to show an awareness that one of your jobs is to not run out of cash. You need to speak intelligently on dilution and valuation. Say why you're raising a given amount, what milestones that money will allow you to achieve, and what milestones come next. 

The Woman Funding Women

Ita Ekpoudom is a New York City-based partner at GingerBread Capital, a growth-stage VC firm that invests in women-led businesses. Its portfolio companies include Brandless, the Riveter, Zola, and Eloquii.

Put your credentials front and center. If you can start a sentence with, "When I was getting my PhD at MIT," it's not bragging. People know that took a long time and a lot of work.

Have up to three asks. If someone says, "Maybe I'm not going to write a check, but what could I do that would be helpful?" you should have three key things in mind.

A pitch deck shouldn't be more than 15 slides, and it should be as visual as possible. Sometimes, you'll see these beautifully done 40-slide decks. No one is going to read all that. 

The Early-Stage Tech Helper

Brett Berson is a partner at First Round Capital, which makes seed-stage investments in tech companies and was the first institutional investor in Uber. Based in San Francisco, Berson is also a founder of Pitch Assist, a program to help First Round's portfolio companies prepare to ask for their next round of funding.

We love it when people open spreadsheets and dashboards in meetings. Early-stage operators should be grounded in the minutiae.

Most breakout startups have a sound core business. If you're pitching nine potential revenue streams in addition to your core business, that is concerning. It implies you may not think the core business is that strong.

Your authentic founding story is important--but 15 minutes on your whole history is a waste.Brett Berson

Ask for other help. At the end of your meeting, every investor will ask, "How can I help?" Ask for references to portfolio com­panies that could become your customers. 

The Cloud-Company Investor

Arif Janmohamed is a Silicon Valley-based partner at Lightspeed Venture Partners. He focuses on cloud and data-center technologies, enterprise mobile, and SaaS firms, like Nutanix, which is now a $6 billion public company.

Don't tell me about your exit strategy. I'm not interested. If you're thinking about the exit strategy, you're not building a company for the long term. I want people who are missionaries, not mercenaries.

If a question is asked, answer it. In many cases, the entrepreneur says, "I have a slide for that in six or seven slides," and we never get to it. Treat the meeting like a conversation, not a pitch.

Be snappy. Entrepreneurs often spend way too long on their demo. Five minutes, tops. 

The Direct-to-Consumer Whisperer

Byron Ling is a principal at Canaan Partners, a firm notable for its gender-diverse investment team and early willingness to invest in consumer companies that are reinventing commerce, education, and entertainment, including Cuyana, the RealReal, and Bird. 

You need to be able to explain your business in 10 words, in 10 seconds. You'd be surprised how often I find myself five minutes into a pitch thinking, "This seems like a great person, but I don't know what they're doing."

A follow-up note that's concise and clear, and can convince me of a point that we'd debated during the pitch, is a really good signal.

From the May 2019 issue of Inc. Magazine