Navigating the Startup Funding Landscape from Maile Keone


According to a new report, recent rounds of tech layoffs are leading to a surge in entrepreneurship as skilled tech workers find themselves on the hunt for their next career move. According to Layoffs.fyiTech, companies laid off at least 160,000 workers in 2022 and more than 100,000 additional people have lost their jobs so far this year. 

This shift in the tech industry is sure to mean increasing competition for startup capital, all the while a looming economic downturn means startup investors are tightening their belts. 

Startup investor and tech executive Maile Keone has seen this ebb and flow of startup capital before. She says the startup funding landscape is constantly changing and emphasizes that increased competition is forcing startups to explore a variety of funding options.

“It’s gotten a lot harder to raise money in many ways. There’s a lot of competition out there that there hasn’t been in the past,” Maile says. “There’s also been a shift in where you access capital and how you get it.”

Maile is the President and CEO of Listen Technologies, an assistive listening and tour system provider. She primarily invests in the technology and real estate sectors. 

On March 8, Maile hosted pitch practice and office hours events for Founders Network members where she provided insights to help startup founders access funding. We talked to her about the changing startup funding landscape and what she looks for when considering potential investments. 

Advice for Entrepreneurs

Maile has a diverse set of experience that includes starting a company from scratch, working for large multinational companies, and everything in between. Today, she uses that experience to mentor other startup founders through her roles as a board member at and the Women Tech Council.

“My love for entrepreneurs comes from the tenacity they have, the guts, the grit,” Maile says. “I get excited by people who have passion.”

Maile is fond of saying that her exits from the two companies she founded wouldn’t have put a child through a semester of college, but she says they were great learning experiences. 

“I have worked with and mentored hundreds of entrepreneurs and the best one piece of advice I can give any of them is know yourself, know if you’re up for the journey. It’s one of the hardest things people do–think of an idea, build a business, try to go out to raise money, and follow through to reach success.

To learn more about startup funding, see if you qualify for membership to join Founders Network.

Funding Trends

When Maile launched her first startup, she did so with the help of a $50,000 loan from her dad. Today, while the startup  funding landscape has changed, and options for funding have increased, she says friends and family remain a common source of capital for early-stage entrepreneurs. According to one report, 38 percent of founders report raising funding from this source. 

“Friends and family are still a great source for people, especially if they can get non-dilutive loans from their friends and family instead of giving away equity,” Maile says. “There’s also tons of accelerators that didn’t exist when I was first out raising money. It seems like every college has an accelerator or a venture fund.”

How to Stand Out

When it comes to making her own investment decisions, Maile looks for entrepreneurs who can easily illustrate the connection between their product, their market, and their customer. 

“A lot of investors ask ‘what problem do you solve?’ For me, it’s one step farther,” Maile says. “You’re solving a problem, but are there a bunch of people waiting on the other end who need that problem solved and how are you going to access them?” 

She also values founders who aren’t easily swayed. 

“My pet peeve is entrepreneurs who aren’t anchored or centered, who take advice from everyone and just pivot, pivot, pivot,” Maile says. “No one knows your business like you do. You have to take all of the advice people give you and filter it. Filter it through what you know, what you know about your business, and your own experience.”

To learn more about startup funding, see if you qualify for membership to join Founders Network.

Share With Your Network

Looking for startup advice, connections, and insights?

Tap into a global network that enables you to answer questions, build relationships, and gain the perspective you need to move faster.
Peer mentorship with fellow tech founders
Pitch practice with Tier 1 VCs
Accelerator grade discounts