When you talk with Annie Evans, one thing becomes immediately clear: entrepreneurship did not just happen to her. It was baked into her upbringing.
Growing up with entrepreneurial parents, Annie learned early that failure was not something to hide from. It was something to laugh about, learn from, and move past. Around the dinner table, stories of ventures that did not work out were shared just as openly as the wins. That environment gave her what she jokingly describes as a very high tolerance for risk, and an optimism that is essential for anyone brave enough to build something from scratch.
That mindset would carry her through multiple businesses, a venture-backed startup, a painful founder fallout, and eventually into the work she does today supporting women founders through Dream Ventures.
TL;DR:
Annie Evans grew up around entrepreneurship, which gave her a high tolerance for risk and failure. After launching multiple businesses, raising venture capital, and experiencing a painful founder fallout, she turned those lessons into Dream Ventures, a firm that helps women founders raise capital through relationship-driven, in-person investing. With support from GoodBread, Annie is scaling her impact while staying rooted in a simple belief: early-stage business works best when it is human.
➡️Listen to the full episode of Breaking Bread: Risk, Resilience, and Raising Capital the Human Way
Making Culture (and Business) Relevant
Annie’s first venture launched in 2008 as an early influencer marketing and events company. The idea was simple but ambitious: make culture feel relevant and accessible to a younger generation.
Rather than positioning museums, performances, and the arts as experiences for a narrow audience, Annie and her partners collaborated with brands to create cultural events that felt social, modern, and engaging. They produced immersive experiences in major cities, working with lifestyle brands and tastemakers to design moments people genuinely wanted to attend and share.
The business ran successfully for several years, but like many early ventures, it had a natural lifecycle. As circumstances evolved, the model no longer aligned with Annie’s direction. She moved on with greater confidence, clarity, and curiosity for what would come next.
A Startup, a Street Corner, and a Big Lesson
In 2012, Annie ran into a frustratingly common problem: trying to book a simple beauty appointment on short notice and realizing how unnecessarily difficult it was. After spending far too long calling around with no luck, she saw the bigger issue. It was not about beauty, it was about access and outdated systems.
That experience sparked her next venture: a platform designed to make booking services like salons and spas fast and seamless, similar to how people reserve restaurants or last-minute travel. She launched the product, onboarded a large network of service providers, built early momentum, and secured seed funding to support growth.
The business expanded and gained traction, but internal challenges began to surface. Misalignment at the leadership level, paired with unclear early agreements, created conflict that eventually brought the company to an end. It was a painful chapter, but it came with lasting lessons.
Before partnering with anyone, do real diligence. Talk to people who have worked with them. Ask hard questions early. Momentum and excitement cannot replace shared values, trust, and clear alignment.
Turning Experience Into Purpose
After Beautified closed, Annie went through a deeply difficult period, one she describes honestly and without sugarcoating. Consulting work eventually took her to Miami, where a fresh environment helped her heal and regain clarity.
When she later joined The Wing in New York, she noticed something striking. Founders were asking the same questions she once had.
How do I raise capital?
What do these terms actually mean?
Am I ready for VC?
Who can I trust?
In 2016, she started Dream Ventures to help answer those questions.
What began as advisory work evolved into something much bigger. Today, Dream Ventures supports founders strategically while Dream Ventures Capital actively invests in women-led companies. The firm leads SPVs, hosts founder-investor events, and helps raise millions in capital through deeply personal, relationship-driven processes.
Investing Is a Human Business
Annie is unapologetic about one thing. She believes early-stage investing should be done in person.
Rather than relying solely on pitch decks and cold introductions, Dream Ventures hosts intimate gatherings in private homes and member-only spaces across the country. Founders tell their stories, investors ask real questions, products are touched and experienced, and trust is built in the room.
“It’s the energy,” Annie shared. “Seeing the founder connect with people, watching their passion, that’s what drives me.”
It is a philosophy rooted in the same belief that drives GoodBread. Business works better when it is human.
Why GoodBread
As Dream Ventures grew, Annie encountered a familiar challenge for many mission-driven businesses. There was plenty of inbound interest, but limited operating capital. Their work is built on long-term upside, which can make short-term cash flow tight.
A loan from GoodBread allowed Annie and her team to invest in growth, including building Fundraise 101, a scalable course designed to teach founders how to raise capital without relying solely on high-touch consulting.
Instead of slowing down, Dream Ventures used flexible financing to move forward.
One Final Lesson
When asked what advice she would leave founders with, Annie did not talk about pitch decks or valuations.
She talked about not taking things personally.
Investors ghost. Partners go quiet. Emails go unanswered. More often than not, it has nothing to do with you or your business and everything to do with what is happening in someone else’s life.
“Stay focused. Stay in your lane. Pursue the yeses,” she said. “The rest is noise.”
Wise words from someone who has lived every side of the founder journey and come out stronger for it.
Join the Conversation
Watch on Spotify: Breaking Bread with Annie Evans: Risk, Resilience, and Raising Capital the Human Way
Share your thoughts or questions: hello@goodbread.net
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Connect with Annie at annie@dreamventures.co
