• 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

Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem

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

Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
Investing

How to Play the Early-Stage Investment ‘Dating Game’

By
Matthew Scanlan
Matthew Scanlan
Down Arrow Button Icon
By
Matthew Scanlan
Matthew Scanlan
Down Arrow Button Icon
February 6, 2016, 1:12 PM ET
Photo: Taylor Weidman
Add Fortune on Google for similar content.

Early-stage investing is like a dating game.

You set up blind coffee meetings, you wait awkwardly, check LinkedIn to make sure you know what they look like, and then you spend an hour seeing if you are compatible.

For me, the process really is this personal. If they like the investment, then we are about to be legally bound to one another (sound familiar?). Once that first meeting takes place, the courting process begins. Many of my earliest investors did not decide to invest until about six months of meetings and dozens of phone calls later. But I get it – if it were my money, I would do the same.

Similarly to dating, a good first date does not mean it is a done deal. Even after six months of good dates, it doesn’t mean you’ll score a deal. Your early-stage investors have to become your biggest and most unconditional supporters. As a caveat, not all investments look alike and some businesses are easier to invest in than others. They are a “sure thing” with a proven executive team, early revenue, and strategic advisers and support. For me, the story was a little different. I was an unproven CEO with little industry experience and no revenue. I had a lot of passion though. My job was to get people as excited as I was about the business opportunity.

You need to view yourself as an investment. No matter how valuable you think your business is, at the end of the day, the investor is investing in you. Entrepreneurs need to really believe in their business or no one else will. They need to be a little delusional and slightly narcissistic. This has been the most valuable perspective I adopted while raising money. An early-stage investor is looking for confidence in the founder, scalability of the business model, and profit margin growth.

But here’s the catch: When an investor finally offers to give you money, you shouldn’t immediately take it. Not every investor will be the right one for you. Turning down $500,000, or even $50,000, is hard, but you need to be able to say “no.” I raised a $1.5 million seed round for Naadam Cashmere, and it took me more than a year. Over that period of time, I turned down more than half a million dollars because either the terms were not correct, the investor wanted to have too much control, or I just didn’t get along with them.

Your early-stage investors become the backbone of your future financing. They become your biggest supporters, open your network to new investors, and provide credibility. So choose wisely. This means that mom and dad are not always the best partners. Family offices and VC firms may want to take too much control. And an angel investor may love the business but not you, and vice-versa.

I pitched at three conferences and met with 35 investors before I ever raised a dime. Since the first investment we brought on, the company has pivoted a lot. I found myself expanding, developing full men’s and women’s collections, and showing during New York Fashion Week. At times, I lost focus of our core differentiators, and I compromised on the things that I told our investors we wouldn’t compromise on. My investors always believed in me, believed in the team I built, and trusted that I could figure it out. That is the bet that makes it exciting to invest in the seed stage of a business. It is a roller-coaster both financially and emotionally. We have flourished because our investors stuck with us, and above all, trusted me.

Like dating, the early days are important. Entrepreneurs need to be careful which investors they select. Not everyone is a fit, but you need to start somewhere. I found that no matter what the variables were, I always had to be the greatest advocate for my business and myself. The truth is my business would not be where it is today if it were not for the investors who took the risk and made a bet on me. Naadam Cashmere, in my opinion of course, is a game-changer that’s disrupting the fashion industry. I have spent two years singing this song and doing the dance. The dividends are calculable, but the experience is priceless.

– Matt Scanlan is the CEO and co-founder of Naadam Cashmere, a socially-conscious brand that sources cashmere from local herders in Mongolia.

About the Author
By Matthew Scanlan
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in

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

Current price of gold as of July 22, 2026
Personal Financegold prices
Current price of gold as of July 22, 2026
By Danny BakstJuly 22, 2026
2 hours ago
t
CommentaryTariffs
Trump’s third tariff tantrum piles more dizzying distractions on top of ever-spiraling failures
By Jeffrey Sonnenfeld and Steven TianJuly 22, 2026
2 hours ago
orson
CommentaryOpenAI
We got California to intervene about OpenAI’s corporate switch from nonprofit status. It’s time for the SEC to come to the table
By Orson Aguilar and Catherine BracyJuly 22, 2026
2 hours ago
A woman observes stock trends on her smartphone while a computer screen displays financial graphs.
NewslettersCFO Daily
Beyond SpaceX: Why great IPOs depend on more than first-day demand
By Sheryl EstradaJuly 22, 2026
3 hours ago
Arrakis cofounder and CEO Rafael Quintanilla.
Startups & VentureVenture Capital
Exclusive: Arrakis, betting AI’s biggest payoff is in industrial sectors not office work, emerges from stealth with $38 million in venture funding
By Jeremy KahnJuly 22, 2026
3 hours ago
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
3 hours 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
19 hours 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
23 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
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
24 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.