I’m joined by VC-backed startup operator, angel investor, author, and podcast host Stef Caldwell. She’s a champion for not just getting women a seat at the table, but actually helping female-owned businesses build their own tables. We talk about some of the reasons why women don’t pursue their big ideas, why she’s so passionate about closing the gender wealth gap, and tips for how to take that first step to starting your business. Stef breaks down the different fundraising options available for entrepreneurs and what to do when you’re feeling lost in a conversation where people are using industry jargon. We also touch on the rise of conscious VCs who believe in creating space for founders to be successful on their own terms and why that shift is so important.
Connect with Stef
Follow Stef on Instagram: @bystefcaldwell
Listen to PM School
Connect with Lori
Lite Pink: @drinklitepink
Earn Your Happy: @earnyourhappy
Girlfriends & Business: @girlfriendsandbusiness
Listen to Girlfriends & Business
Stef Caldwell is a personal development author, vc-backed startup operator and angel investor who specializes in helping start ups & high-growth companies develop and generate revenue in new and existing sales channels. Stef has a proven track record in breaking into and closing business at the highest levels of F500 companies and commercial markets. Stef has expertise in developing strategic executive relationships, and negotiating complex deals, making her an asset to business development teams charged with building new revenue channels from scratch within aggressive timeframes and/or optimizing existing channels.
Since childhood, when she wrote a letter to the White House about race and class discrimination in her third grade classroom, she’s been focused on how she can make an outsized impact & make the world a more equitable place for all. The culmination of a lifetime of focusing on how to make the world a better place translates directly into her work as an author, investor and mentor to women consumer and tech. She is the author of ManifestHer – The Ambitious Woman’s Guide to Getting Unstuck, Navigating Ambiguity and Manifesting Your Biggest Dreams, which was published in Fall of 2020 and received praise from Best-Selling Authors Kim Scott (Radical Candor), Amber Rae (Choose Wonder Over Worry), Lori Harder (A Tribe Called Bliss) & Team USA Gold-Medalist, Lauren Doyle.
By day, she is the Head of Business Development & Partnerships at CircleUp, a top FinTech company using Al to make venture capital more equitable & scaling access to capital to epic entrepreneurs so they can thrive. Their top performing venture fund is both diverse (>50% female founders & >35% minority founders) and has achieved top performance marks.
By night, she is the host of PM School Podcast, an inspiring, “how I’m building this” style podcast inspiring the next generation of women entrepreneurs by bringing them behind the scenes with inspiring founders to hear the stories of how they ideated, started, capitalized and scaled their businesses.
Discussion Questions & Episode Highlights
( 1:06 ) Welcome back to Earn Your Happy. Today, Lori is joined by Stef Caldwell.
( 2:57 ) Stef joins the conversation.
( 4:24 ) Lori asks Stef, “Tell me what your day-to-day looks like and why exactly it is that you are in these details of women and business.”
( 6:19 ) Lori asks Stef, “How much do you take into consideration the data, but then how much do you also feel out in the world for companies and decision making as also kind of gut feeling and kind of looking at the future of what we think trends are and things like that?”
( 9:44 ) Lori asks Stef, “What do you think are some of the reasons when you really get into the nitty gritty that women don’t start businesses?”
( 10:47 ) Lori says to Stef, “You also talked about women are starting 40% of business, but I’m gonna let you roll with some of your stats. So you go to town.”
( 11:39 ) Lori asks Stef, “Women are starting 40% of businesses generating 2 trillion in American revenue, but that’s less than 4.5% of total revenues. Tell me why this matters to you.”
( 13:43 ) Lori shouts out one of today’s sponsors, ISSU.
( 16:01 ) Lori asks Stef, “Right now, if you were teaching the next generation of women exactly what to do, what examples would you use? And what would you tell them to do with their money?”
( 17:37 ) Lori asks Stef, “How do we get all of this info into some beautiful bite-sized information to really have women understand what’s going on and why we need to invest, why we need to start businesses, and why we need to make more money than what we actually think right now as possible for ourselves?”
( 21:16 ) Lori asks Stef, “Let’s start bringing that conversation around to what does this look like for a woman who’s like, oh, I have an idea. Maybe a beauty product, maybe it’s jewelry, maybe it’s tech, maybe it’s something that could change the world, but just feels so far out of your reach right now. What are your first steps on that?”
( 24:49 ) Lori asks Stef, “So the initial spot of figuring that out is just literally ask all the questions. What’s our next step?”
( 25:56 ) Lori shouts out the other sponsor of today’s episode, Bombas.
( 29:09 ) Lori asks Stef, “Do you want to chat about some different ways to raise money?”
( 33:42 ) Lori asks Stef, “If I get this money from people now, I literally am expected to not sleep to not take care of myself to be seen working 24/7, even if that work is total shit. Tell me about this conversation on your end. Are you hearing any of this? What are your thoughts on it?”
( 40:20 ) Lori asks Stef, “If I don’t have the people to ask, I don’t have the network, I don’t have the confidence, where could we start to at least not bench ourselves before the game has begun?”
( 44:59 ) Lori asks Stef, “What are some things we did not cover, if anything?”
( 48:27 ) Lori asks Stef, “Any last words for our listeners that you want to add?”
( 49:00 ) Follow @bystefcaldwell, tag her in your story, and let her know what your biggest takeaway from this episode was.