Founding companies is a high risk, high reward scenario. But many women don’t realize just how much more money they could be making, even by running a low-risk venture. Women still make 87 cents for every dollar that men make — and that’s the most narrow gap between Asian women and white men. White, Black, Native American and and Latina women experience an even more dramatic wage gap. I (Claire) will never stop telling women to try freelancing. And freelancing is a gateway to even bolder pursuits. My first year freelancing, I doubled the income I made in my last full time position. I have so many conversations with talented women with skillsets prime for freelancing who are stuck in jobs that work them to the bone for 40k dollars /year. This is unacceptable. Not just that companies pay women in their 30s (or anyone, for that matter) 40k dollars per year, but that these women don’t see that they’re worth way more.
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Claire Glisson and Liz Heinberg.
Claire Glisson, a startup brand strategist, and Liz Heinberg, a veteran tech founder are the cofounders of Ditto, a SaaS startup that brings an Agile approach to managing outsourced work. They have collaborated on multiple tech startups, including Ditto and Hum, where they both currently work full time. Liz & Claire continue to freelance together, in addition to working at the two tech companies. Suffice it to say, they’re pretty busy… and definitely enjoy working together. Ditto was inspired by a freelance project gone wrong… more on that in the next few questions!
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Claire: I just kind of fell into it. I went to a big name advertising school, full of huge personalities and an impressive alumni list. I quickly realized I loved the work, but not the culture of the industry, and while my classmates took jobs with big brands and highly regarded creative agencies, I took a marketing job with a boutique hospitality company. This was my first “startup” experience. I loved the number of hats I tried on during my time on their marketing team, and the space I was given to mold the marketing operations. Fast forward a few roles, a stint in freelancing, and many lessons about doing business learned. My career really took off when I moved to Amsterdam and started freelancing full time. I worked with tons of young companies in Europe and in the US, helping to grow and scale their marketing operations.
Liz: My career path has definitely been a little curvy! Once upon a time, I thought I wanted to train horses, but I tried that on for size and quickly realized that the dream was better than the reality. I ended up back in grad school, studying Creative Brand Management, and discovered that building a brand strategy was just plain fun for me — and I was good at it. After graduating, I headed up the marketing department for a small business. There, I discovered two things: I really love naming stuff, and I also really love the early “shaping” of brands and companies. Along the way, I also developed an entrepreneurial itch and became super interested in software. So I made the leap, founded a mobile app startup (because of course… that’s what everyone does, right?), and self-educated my way into where I am now: working as the Chief Product Officer at one tech startup, building up another tech startup on the side, and still doing some naming and branding work, too. In case you were wondering, the mobile app failed. But boy, did I learn a lot.
Can you share the most interesting story that happened to you since you began your career?
In 2018, we collaborated on a freelance project for a friend-of-a-colleague and never got paid. We made some stupid choices — working on a handshake agreement and abandoning our CYA processes to meet the client’s quick turn deadline. We got sad, we got mad, we sent legal letters, and 3 years later, we still haven’t seen payment. But the silver lining was that we got the idea for Ditto. We did some research and quickly realized that our situation was not unique. On average, each freelancer misses out on 6k dollars every year in unpaid invoices. We set out to change that. Our core mission is to realign the imbalance of power between freelancers and clients. Our initial idea for solving this problem involves automating and normalizing the process of holding payments in escrow for contract work.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Claire: Early in my career I sent a very stupid email after my last day at the company. I had a stressful day of wrapping up projects and tying up loose ends, followed by a stressful evening of preparing for a major move. I got a ping on my phone (where my work email was still installed) from a coworker asking me to update credit card billing on a company account. My delirious brain thought this was some sort of a joke, as they knew I’d just finished my last day, I didn’t even have a computer, and their ask was something they could easily do themselves. My response was incredibly stupid: “Lol, not unless you want me to send an invoice- I’m not on payroll anymore!” As you might imagine, the coworker forwarded the email to my former boss and chaos ensued. There were threats of withholding future recommendations, questions about how I could be so crass and tasteless, and a general feeling that I’d tarnished all the good work I’d accomplished in the 2 years I’d been there.
After the fact, I’m sobered. I’ll never shoot off emails without thinking, especially when I’m exhausted and shouldn’t be work emailing anyway. I’m also a little indignant. I cried about this for days, but the truth was, I did GREAT work at that company, and my boss absolutely knew me well enough to see this silly email for what it was and react accordingly. I’m embarrassed, and I still hate that I left the company on a sour note, but in the aftermath, I was made to feel like a classless jerk. With time, I now know that’s not true. I’m embarrassed, but I’m not ashamed.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Claire: Honestly, Liz has been the best thing to happen to my career. I call her my “friendtor” = friend and mentor. We met in 2016 when we lived in the same town — Charlottesville, VA. She and I attended the same grad school (at different times) and she was looking for a cofounder for one of her startup projects. I didn’t fit what she was looking for, but I reached out, realizing we lived in the same city. Fast forward many many work projects, countless spin classes, and one transatlantic move and I feel like I have a work wife for life. She’s seen the good, bad and ugly of my career, including the infamous email story I just told. Having someone like this in your corner is so essential, especially as women in business. We talk strategy about everything from talking spouses through the trials of startup life to navigating workplace politics, to personal stuff like how having children impacts career plans.
Liz: Well, the feeling Claire shares is mutual. She’s my “friendtor,” too! I love working with her and have a ton of respect for her brainpower, and for who she is as a person. I feel really fortunate and grateful to have found such an awesome partner — someone who both challenges and energizes me.
I don’t know that I would have known how to help lift Claire up, though, if it hadn’t been done for me. I met Mark Speece when I was working as a director of marketing and I had fallen into naming the company’s products. I learned of Mark (and about “naming” as an actual profession) from a Brandcenter professor who connected the two of us. Mark validated that yes, I was good at this naming thing, and then he proceeded to basically bring me under his wing. He somehow simultaneously makes me feel 100% heard and respected, and yet also teaches me so much. In client presentations, he’s very careful to make sure that we come across as a team of equals, and that’s something I really appreciate. I still do most of my naming work with him.
Maybe the moral of my story is: you help make your own luck. As an introvert who hates networking, it wasn’t super-comfortable for me to make either of these connections… but WOW am I glad that I did.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
Liz: Well, speaking of introversion… I’d recommend Quiet: The Power of Introverts in a World That Can’t Stop Talking, by Susan Cain.
As an introvert, this book was transformational in helping me learn to appreciate my own unique strengths, and in shaping my approach to leadership. It made me consider more deeply which skills I need to develop in order to be an effective leader — and which I don’t. Our society often celebrates extroverts, especially in leadership positions, and this book helped me realize that my introversion isn’t something I need to “overcome” in order to be a leader. In my opinion, it’s a must-read for people who are more introverted, but it would also be beneficial for extroverts who’d like to better understand and perhaps appreciate others’ personalities and challenges.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
Liz: I have a quote on my Notion “Life Dashboard” so that I will see it every day. It simply says “what you do is who you are.” It’s actually the title of a book I read by Ben Horowitz about company culture. These words really resonated with me at this time in my life. I’m juggling so much, and for a period of time, I wasn’t doing a very good job on the relationship side of things. This quote reminds me that just because I FEEL loving thoughts toward my husband doesn’t mean that HE feels it — unless I do things that help communicate my affection. And unless I DO the things on my various to-do lists, they’re just good intentions. I’m not actually going to be able to build Ditto, for example, without taking actions — lots and lots of them. If months were to go by without any effort spent on Ditto, could I really call myself a founder and feel good about that? The same goes for personal relationships — I can’t be a loving spouse without putting my energy towards being one. I want my perception of myself — and the person I want to help myself grow to become — to match up with the way I spend my time every day.
How have you used your success to make the world a better place?
We believe that our current project, Ditto, will make the world a better place for people who do outsourced/contract work. As we mentioned in our origin story, there is a gross imbalance of power between freelancers and their clients. Agency freelancers often wait 30 to 90 days to get paid after their work is completed, essentially floating the bill while agencies wait for their clients to pay them. Freelancers also struggle with scope creep, or, clients asking for more and more without additional budget. But we also learned that clients have pain points of their own. It can be difficult for clients to get a transparent look at how the project is progressing against the original quoted budget, and freelancers are notorious for submitting late invoices, which throws off accounting. Ditto addresses all of these points by reimagining the way clients and contractors work — from proposal to contracting to project management to payments. Ditto takes best practices from Agile methodology to make work more flexible, with features like dynamic project scoping (adding small phases + associated payments in real time), dynamic contracts (that update alongside the scope/ project flow) and of course, taking escrow payments upfront that align with each small phase of work.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
There are a number of factors “holding women back,” all of which we go into in more detail in subsequent questions, and I think the primary reason probably varies with the woman. Founding can feel both very difficult and also very risky; most successful entrepreneurs will tell you that there’s no way they could have made it without their support network. It seems that (again, for a number of reasons) women have historically played more of a supporting than a starring role. It takes time to change that… and it IS time to change that!
Can you share with our readers what you are doing to help empower women to become founders?
Freelancing is a great way for women to get a taste of entrepreneurialism. Many women start freelancing on the side, or after taking a break from the corporate world while having children, or to carry them through lapses in full time employment. Of course, many others boldly and consciously decide to quit working for someone else and start working for themselves. We’ve learned that female freelancers have the hardest time talking about payment with clients. They chronically lowball their rates, they don’t feel confident negotiating higher pay, and they are most likely to prioritize a working relationship over a solid working agreement that mitigates risk. We created Ditto to empower freelancers to regain control of scope and payment conversations. Ditto restores the balance of power in the contractor — client relationship. For women who freelance, Ditto automates away the admin, so they can focus fully on the work and not the things that might go wrong. It’s a much smaller leap from freelancer to founder (of a small agency or consultancy, for example) than from salaried employee to founder!
This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
• We don’t need to tell you why diversity is so important in business. In startups, it’s very rare to find young teams that aren’t full of your typical Silicon Valley dude-bros, much less diverse founders. It’s human nature to build things (companies) to solve problems you have experienced first hand. When women and minorities aren’t part of these founding teams, their experiences aren’t accounted for. Viable market opportunities aside, the moral and ethical implications are clear. History has proven that minorities struggle, and experience the world in ways that heteronormative, able-bodied white men don’t — why are we still building businesses that only solve problems via their singular lens?
• Founding companies is a high risk, high reward scenario. But many women don’t realize just how much more money they could be making, even by running a low-risk venture. Women still make 87 cents for every dollar that men make — and that’s the most narrow gap between Asian women and white men. White, Black, Native American and and Latina women experience an even more dramatic wage gap. I (Claire) will never stop telling women to try freelancing. And freelancing is a gateway to even bolder pursuits. My first year freelancing, I doubled the income I made in my last full time position. I have so many conversations with talented women with skillsets prime for freelancing who are stuck in jobs that work them to the bone for 40k dollars/year. This is unacceptable. Not just that companies pay women in their 30s (or anyone, for that matter) 40k dollars per year, but that these women don’t see that they’re worth way more.
• Being a founder is empowering. Even in a little early stage, non VC funded startup like ours, it’s an amazing feeling to say “we made this, and people want this because it helps them.” You’ll never feel the same sense of agency and ownership over your work as you’ll feel when starting your own company. Many women find that sense of self and pride in ownership over their home life, while men tend to find that feeling at work. There’s nothing wrong with putting your whole self into building a home and a family, but there’s something that feels extra special about finding ownership in a path that hasn’t traditionally been encouraged for women.
Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.
• Stop the narrative that “women can have it all.” It’s a concept with longstanding roots in feminist credo, but today functions as a blanket term for “women can have a career and a family.” It seems empowering at first glance, but it’s actually a dangerous trope, because (normative, white) men already have, and always have had it all. And it hasn’t been nearly as hard for them to do it. When you say “women can have it all” it’s hard not to imagine the other side of that coin– a sense of looming failure. It’s a subliminal crime against feminism if women can’t reconcile their personal and professional lives, or ~worse~: decide not to have children, or not to have a career at all. Having it all feels nebulous, and impossible, especially when studies pretty much unanimously show that women are still penalized for pregnancy at work, and still bear the mental and physical load at home. Really, we should be encouraging unique and individual paths, and celebrating success that women find when leaning into these interests and strengths. Because no one really wants “it all.” Please stop telling us we do.
• Partners, please help pick up the slack at home. Speaking of women bearing the load at home, women can’t and won’t become founders until there’s balance at home. All seasoned founders know that work towards great new ideas, and personal pursuits happens when you’re off the clock. Except many women (especially mothers) rarely find themselves off the clock. No matter how high powered your job, when you get home, dinner needs to be made, laundry needs to be folded, and the house needs to be cleaned. This type of work almost always falls to women, as does the mental labor that comes with it. Women become de facto household project managers who spend lots of time planning dinner menus for the week, scheduling appointments, shopping, and constantly reminding everyone in the household where they need to be and what they need to do. Does it sound exhausting? Because it is.
Luckily my (Claire) partner has always been an excellent contributor to physical household labor. We almost always cook, clean and run household errands together. Shout out to my Parents In Law for the excellent training. In the past 2 years, though, we’ve had to shift our allocation of mental labor. He was in a rigorous PhD program when we were first married, and I took on the lion’s share of household planning. When we moved to Amsterdam, my freelance career took off, and his slowed down (in a good, normal job kind of way). All of a sudden he was thrust into planning our weekly dinner menus and managing the minutiae of the household. We had to talk through it, because to him, it seemed like an inequitable situation at first (it wasn’t). In reality, these were all the things I had championed for the majority of our marriage- things he didn’t even see as labor, until he had to do them himself.
• A thriving family and a high-powered career shouldn’t be mutually exclusive. There’s an overlap between peak childbearing years and the time in a woman’s career when she’s most ambitious and ready for high-growth pursuits. Unfortunately, the demands of startups and the demands of motherhood often don’t play well together. But it doesn’t have to be that way. Family-friendly cultural shifts are happening (see normalizing paternal leave for fathers, expanded family friendly policies that go beyond traditional pregnancy allowances, etc), but corporate America can do more. And startup culture can definitely do more. Getting more women into high powered positions will help to bring on these much needed cultural changes. Just as men don’t give a second thought to telling their boss they’ll need multiple weeks off to recover from major surgery, women should never be nervous about, or feel like they have to apologize for pregnancy.
• Seeing is believing — promote women and support women. It’s no secret that role models are powerful. The lucky ones among us have had the chance to see a bad-ass woman in action; to observe and learn from her, and if we’re really fortunate, to have been mentored by her. But it’s not just about having women as role models — it’s also about normalizing womens’ places on executive teams and as the leaders of companies. I always notice when a company has female leaders — and that, in itself, is the problem! Women in leadership positions are still rare enough that they’re noteworthy. This is about women lifting each other up, but there’s also a huge role for male advocates to play here. Men need to encourage women to swing bigger, and then give them the room to step up. I’ve (Liz) actually had a male colleague encourage me to “think like a man” when asking for a position and salary… and again, I wish it weren’t the case that I knew exactly what he meant. This is one of the reasons entrepreneurship is so exciting for gender equality — women have the chance to succeed and stand out, completely on their own merit.
• Fund women. It’s hard to make something from nothing, with no resources. This is something we’ve lived first-hand! Bootstrapping (especially while trying to earn a living on the side) is darn difficult. If we were able to get our hands on a bunch of VC money in order to have the freedom to relentlessly pursue nothing but our startup, we’d be playing a whole different ball game right now. But it’s well-known that VC money is hard to raise, and that it predominantly flows through connections and networks. As a result, those of us who don’t have access to “warm leads’’ brokered through the (predominantly young, white) boys’ club are left out in the cold. Crunchbase data show that not only did total funding to female-led startups fall this year, but the proportion of dollars to female-only founders also declined, to 2.3 percent, compared to 2.8 percent in 2019. I mean, ouch! Funding is effectively another kind of gate-keeping, and these gates need to be broken down, alongside glass ceilings.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
We live in a time where the environment poses one of the greatest threats to the future of our humanity. We’ve ignored it for so long, and we need to take care of our home — it’s the only one we have. If we could start any movement (that we’re clearly not qualified to start) it would be one marked by great corporate responsibility to take care of our planet. Profits be damned, the giants of capitalism have the best opportunity to ameliorate climate change. Until companies like Apple stop creating products with planned obsolescence (aka, planning for mass exodus of plastics into the environment), no amount of personal responsibility to stop using straws or eat less meat will make a difference. Don’t get us wrong, we’d love to see expanded personal commitments to improving environmental factors. But the big companies have the best opportunity, and greatest responsibility to make impactful changes.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
We’re really inspired by Basecamp. We love their products, their ethos, and their approach to building a company. So it’d be pretty cool (but also a little scary?) to chat with Jason Fried.
How can our readers further follow your work online?
Check out our website at workwithditto.com! We’re in the process of building out a bunch of (free) resources for freelancers and solopreneurs, so sign up to share your email address if you want to be kept in the loop.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.