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

Trendingnow

1

Analysts expected oil to surge above $200 but China has quietly kept prices half of that—and can’t for much longer

2

Corporate America has been draining the world's water. Matt Damon's new campaign calls on Gap, Starbucks, and Amazon to help give it back

3

Marc Lore’s robots make 500 burrito bowls an hour. A human can make 45

1

Analysts expected oil to surge above $200 but China has quietly kept prices half of that—and can’t for much longer

2

Corporate America has been draining the world's water. Matt Damon's new campaign calls on Gap, Starbucks, and Amazon to help give it back

3

Marc Lore’s robots make 500 burrito bowls an hour. A human can make 45
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

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

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
  • Pinterest icon

Latest in

defense
PoliticsDefense
Trump says Europe freeloads on defense. Britain’s own (former) Defense Secretary just agreed
By Jill Lawless, Danica Kirka and The Associated PressJune 11, 2026
4 hours ago
Why is it so hard to get ROI from AI? Because building from first principles isn’t easy
NewslettersEye on AI
Why is it so hard to get ROI from AI? Because building from first principles isn’t easy
By Jeremy KahnJune 11, 2026
7 hours ago
SpaceX lowballed its bankers on fees. Goldman Sachs has another way to win big
Startups & VentureFinance
SpaceX lowballed its bankers on fees. Goldman Sachs has another way to win big
By Shawn TullyJune 11, 2026
8 hours ago
Traders work on the floor of the New York Stock Exchange during afternoon trading on June 10, 2026 in New York City.
InvestingWall Street
Bank of America told investors to ‘take profits.’ Then the Nasdaq fell 7%
By Eva RoytburgJune 11, 2026
8 hours ago
Three ways that Asia’s enterprises are adopting AI—and where they are falling behind
CommentaryOracle
Three ways that Asia’s enterprises are adopting AI—and where they are falling behind
By Garrett IlgJune 11, 2026
9 hours ago
Full Coverage Car Insurance: What It Covers, What It Costs, and Who Needs It
Personal FinanceInsurance
Full Coverage Car Insurance: What It Covers, What It Costs, and Who Needs It
By Joseph HostetlerJune 11, 2026
9 hours ago

Most Popular

Analysts expected oil to surge above $200 but China has quietly kept prices half of that—and can’t for much longer
Energy
Analysts expected oil to surge above $200 but China has quietly kept prices half of that—and can’t for much longer
By Sasha RogelbergJune 10, 2026
1 day ago
Corporate America has been draining the world's water. Matt Damon's new campaign calls on Gap, Starbucks, and Amazon to help give it back
Environment
Corporate America has been draining the world's water. Matt Damon's new campaign calls on Gap, Starbucks, and Amazon to help give it back
By Catherina GioinoJune 9, 2026
3 days ago
Marc Lore’s robots make 500 burrito bowls an hour. A human can make 45
Innovation
Marc Lore’s robots make 500 burrito bowls an hour. A human can make 45
By Amanda GerutJune 9, 2026
2 days ago
Current price of oil as of June 11, 2026
Personal Finance
Current price of oil as of June 11, 2026
By Joseph HostetlerJune 11, 2026
17 hours ago
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
Success
Costco CEO Ron Vachris rose from forklift driver to the C-suite without a college degree: ‘Don’t chase a title’ is the career advice that got him there
By Preston ForeJune 8, 2026
4 days ago
Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
Asia
Pentagon accuses Alibaba, Baidu and BYD, three of China's biggest companies, of supporting the Chinese military
By Kate O'Keeffe and BloombergJune 8, 2026
3 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.