• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
Commentary

Why You Should Never Take an Investor to Coffee

By
Andy Lark
Andy Lark
and
Bethany Cianciolo
Bethany Cianciolo
Down Arrow Button Icon
By
Andy Lark
Andy Lark
and
Bethany Cianciolo
Bethany Cianciolo
Down Arrow Button Icon
February 6, 2016, 11:00 AM ET
Courtesy of Xero
Add Fortune on Google for similar content.

The Entrepreneur Insider network is an online community where the most thoughtful and influential people in America’s startup scene contribute answers to timely questions about entrepreneurship and careers. Today’s answer to the question “What’s the best way to pitch a startup idea to investors?” is written by Andy Lark, CMO of Xero.

After sitting through hundreds of pitches and listening to requests for money, advice, and help, you learn a few things. Mostly though, you develop a mix of empathy and frustration, punctuated by occasional delight.

There is no shortage of advice and tips out there on how to raise money for your big idea, so here’s some thoughts from the other side of the table:

Rarely does anything start with “a coffee”
Most of us are caffeinated enough. Spare the opening, “Can I buy you a coffee?” Instead, just come clean with what you’re after. You’ll save yourself days of meetings with people not in the market to invest, not interested in your sector, or just too time-taxed to give your idea the attention it is due.

See also: How to Avoid a Startup Failure

Use a rifle, not a shotgun
While most founders will have a standard pitch deck ready to go for their investor meetings, you need to adjust each presentation to fit the audience. Too many people pitch far and wide without addressing the particular investor sitting in front of them. Each investor will have varying focuses, mandates, and interests. Do your research and appeal to those nuances.

If you won’t bleed for it, a good investor won’t invest in it
Above almost anything else, investors are looking for unequivocal commitment and passion. If you can’t demonstrate that this is your dying purpose, why would an investor risk his or her hard-earned cash on you? One thing Xero founder Rod Drury often speaks about is “bleeding blue.” Building a beautiful cloud accounting system is almost all he thinks about—it’s in his veins. When asked if he would like to invest in a company, his response is clear: “Sorry, I’m all in on Xero.”

Smart money is better than dumb money
But some money is better than none. Sure, there may be people who can’t add substantial value to your business, but that doesn’t mean those investors—or their money—is dumb. Be thoughtful about what investment you take and pitch for the relationship you’d like to have. Not all investors need be equal.

Engage from the outset
You need to be compelling. If you’re not, either partner with someone who is or learn to command a room. A big part of this is being subject-matter deep: Do your homework.

One way to engage attention is through conversation. If you’re just speaking at everyone you’ll get less interest than if you’re speaking with them.

 

Figure out if you’ve earned the right to pitch
Just because you’ve got a meeting with an investor doesn’t mean you’ve earned the right to pitch them. In fact, if it’s a meet-and-greet type situation, you could actually do yourself more harm by coming on too strong, too early. Over-pitching an investor is like being on a date where all the other person does is speak about how good he or she is. If you find yourself doing that, you’re unlikely to get a call back. Keep your pitch deck short, address any concerns you think they may have upfront, and be receptive to feedback.

Surround the opportunity
Your pitch doesn’t end when you stop talking. You need to lead the process, bundle up a few action points, and give your audience their next steps. This can include pointing them to where they can go for references, data points, or customer testimonials. If you do your job well, they will do their job well, the first step of which is fact-checking everything you said.

Don’t oversell
Seriously, no stretching the truth, presenting warped metrics, or lying. It’s likely this isn’t the first pitch your audience has heard, and if you start off sounding a little iffy, alarm bells will sound. Tell the truth and spotlight the opportunity with integrity. Too many entrepreneurs lie or base assertions on lousy facts. Google search results will slap you unconscious.

Being confident and honest. Targeting your presentation to your audience and handling any concerns you think they may have upfront will help you build solid investor relations.

About the Authors
By Andy Lark
See full bioRight Arrow Button Icon
By Bethany Cianciolo
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Commentary

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in Commentary

ls
Commentarybooks
Confessions of an award-winning AI memoirist — the ‘slop’ debate isn’t really about good writing, and you know it
By Luke StoffelJuly 22, 2026
11 minutes ago
b
Commentarythe future of work
Manpower President: The future of work question that even CEOs can’t answer
By Becky FrankiewiczJuly 22, 2026
11 minutes ago
k
Commentarypower
What I keep hearing from Fortune 500 CEOs: ‘We have no idea what we’re actually paying for power’
By Kiran BhatrajuJuly 21, 2026
1 day ago
Bolt CEO Ryan Breslow
CommentaryHuman resources
The CEO who fired HR was right. About the wrong thing.
By KeyAnna SchmiedlJuly 21, 2026
1 day ago
ford
Commentary250 Years of Innovation
Alliance for America’s Skilled Trades: Skilled trades shaped America’s past. Here’s how they can build America’s future
By Jim Farley, Linda Hubbard, Bayo Ogunlesi and Ruth PoratJuly 21, 2026
1 day ago
Sumeet Agrawal is VP of Product Management (Data, AI Governance & Context Engineering for Agentic Systems) at Salesforce.
CommentaryAI agents
Salesforce VP on the leaky AI pipeline: why cheaper tokens won’t fix enterprise AI
By Sumeet AgrawalJuly 20, 2026
2 days ago

Most Popular

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
Success
Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
By Sasha RogelbergJuly 20, 2026
2 days ago
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
Cybersecurity
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
By Jeremy Kahn and Emily ForliniJuly 21, 2026
16 hours ago
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
Success
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
By Sydney LakeJuly 20, 2026
2 days ago
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
AI
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
By Eva RoytburgJuly 21, 2026
19 hours ago
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
Success
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
By Emma BurleighJuly 21, 2026
21 hours ago
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
AI
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
By Jason MaJuly 18, 2026
4 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.