Lindsay Tia Reilly, owner of a successful handbag and accessories line, talks about how being brave in business led to success.

Benefits of Taking Risks in Business | 28 Carrots

Benefits of Taking Risks in Business

When Lindsay Tia Reilly started making handbags at age 14, she knew she had found her passion. When she did her first manufacture run while still in college, she knew she had found a business.

For many people, the magic formula of finding passion in their career never materializes. But for entrepreneurs, the two go hand-in-hand. For Reilly, and many businesswomen of the same mold, loving what she does is as important as what she does.

“I’m not really selling a handbag,” she says. “I’m selling more than that. It’s what I truly believe in.”


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One of Reilly’s most popular lines – the Bravery Brand – is a patriotic design inspired by men and women in the military.

“When you buy one of my handbags, you are supporting men and women in the troops, and something that is American-made,” she says. “It’s a far bigger dream than the bag itself. It’s really building something.”

Reilly recently shared her success story with the 28 Carrots blog. She explains that the turning point was learning the importance of taking risks, and seeing firsthand how bravery in business can pay off.

Some of Reilly’s most important – and fruitful – risks include:

  • First manufacture run: For years, Lindsay made her own bags and sold them at Christmas shows and expos. While in school at Lasell College, she launched a website to sell them online and her need increased. Letting go of control over the manufacture of her bags was an important first step. Her first run produced 100 bags.
  • Opening her first storefront: After graduation, Reilly opened her first store in Abington. “I had no idea what I was doing,” she says. “But with everything else I’ve done, I figured it out.”
  • Learning to pitch her line: As a young entrepreneur, Reilly had to master the art of public speaking and 1:1 pitches. “When you have no choice, you have to do it,” she explains. “I needed to be able to walk into a store and say, ‘I’m Lindsay Tia and I make these handbags…’ Now I can speak in front of 500 people and it doesn’t even faze me.”
  • Investing in the Bravery Bag line: When Reilly conceived of the Bravery design, she took a big risk with a huge order. She decided to throw a party for 40 people to help raise money for the troops. With only 3-4 weeks of planning, her small party morphed into a large-scale event with 400 attendees at the Granite Links ballroom in Quincy. She raised $20,000 for the USO as a result.


Meet Reilly May 4 at InnovateHER

Reilly is among five inspirational women entrepreneurs speaking at this week’s InnovateHER networking event at the Willowdale Estate. Hear her share her story firsthand, and enjoy an additional 16 lightning talks and four business pitches from women just like you. Learn more about InnovateHER and buy tickets – while they last!