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A pair of Brandcenter alumnae hit the right note to be crowned the 2021 VCU Alumni Pitch Competition champion

Event host Faith Wilkerson, Ed.D. (B.S.’03/MC; M.Ed.’05/E; Ed.D.’15/E) (left), winner Elizabeth Heinberg (M.S.’08/B) and event organizer Latisha Taylor Smart

In 2018, Elizabeth Heinberg (M.S.’08/B), a veteran tech founder, and Claire Glisson (M.S.’16/B), a startup brand strategist, collaborated on a freelance project for a friend-of-a-colleague and never got paid. In hindsight, they admit working on a handshake agreement and abandoning their CYA processes to meet the client’s quick turn deadline wasn’t the best decision. The silver lining was that they got the idea for Ditto, a SaaS startup that brings an Agile approach to managing outsourced work.

“We did some research and quickly realized that our situation was not unique,” the partners said in a March 2021 interview with Authority Magazine. “On average, each freelancer misses out on $6k 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.”

Heinberg and Glisson have pitched their startup many times but lost many of the competitions. “You just have to keep going,” Heinberg says. “We believe in it, and that matters.”

Their perseverance, and luck, changed Nov. 11 when Heinberg presented at and won the 2021 VCU Alumni Pitch Competition. “We’ve been bootstrapping, putting our own money toward Ditto, so this feels like a real turning point for us,” Heinberg says.

Latisha Taylor Smart, director of alumni career and personal development for VCU Alumni and organizer of the annual pitch competition, caught up with Heinberg recently, who was still riding high from her win.

Share a little about your career background, and how that led to the inspiration of you creating Ditto.

A few years after graduating from the VCU Brandcenter, I got a job as a director of marketing for a sleep products company. I was there for eight years or so, but I have a real entrepreneurial itch, so I started to do some stuff on the side. I started off with a mobile app that I developed called Simili that helped people decide where to eat and when to meet. I was tired of trying to get together with my friends and having everyone say, “Where do you want to go?” “I don’t know, where do you want to go?” So I created an app, and I hired a developer and spent a lot of money and learned a lot of expensive lessons about entrepreneurship and startups. At some point in there, I left my full-time job and started to do brand strategy and verbal identity freelance work.

Claire and I met on the VCU Brandcenter alumni Facebook group and had already partnered on other projects when we had a new one come in. The client was a friend of a friend so we were not too concerned about putting a contract in place. We did great work and then the client never paid and the company ended up dissolving. We started to do some research and found out that it actually happens to a lot of freelancers.

We felt like there was a real opportunity to make sure that both sides get what they’re hoping to get out of the arrangement. If you’re at the stage where you’re looking back at the contract, well, that’s too late. Things already went very badly. If you could be more proactive, instead of reactive, it would be better for everyone, not just freelancers but better for clients, too.

So we started to work on Ditto. For freelancers, Ditto streamlines administrative tasks and ensures prompt payment via an escrow system. This both ensures against nonpayment or late payment and also smoothes out a typically erratic income stream. For clients, it provides a time-saving structure and system for interacting with external resources, and clear visibility into where the project stands at all times via a client portal.

I’ve been working on Ditto now for almost three years, and Claire and I were joined by two developers who had worked on my first startup. They are co-founders, too, so this time instead of paying for development, they are actually part of the team, but that has meant that we’ve gone a little bit slower because we’ve all been working part time on Ditto.

What brought you and Claire together to create Ditto? How did that mashup happen?

She’s wonderful, and I feel really lucky to have found her, and she sort of found me. She’s 10 years behind me so we didn’t overlap at school but found each other on the Brandcenter alumni Facebook group when I posted that I was looking for someone to help me on the technical side. This was for Simili, the previous startup, and she responded and said, “I’m not a technical person, but I really like brainstorming, and I’d be happy to.” And she said, “I feel like I’m not getting enough of it at my job. I feel like my brain was more creatively stimulated while I was in school, and that I’m losing it.” We started getting together and it was really invigorating and we just hit it off. We imagine doing many projects together in the future.

Right now she’s in Amsterdam, which was why she couldn’t come to the pitch competition. Her husband is an academic and will be in Amsterdam for a couple of years.

Did you always know that your career path would lead you here, into this entrepreneurship/startup life?

No, definitely not. I still do a lot of marketing and branding, and I really enjoy that. That’s what I went to school for. But as I said, I had that itch, and I just wanted to try it. I’m really surprised that I’m basically a tech entrepreneur. Growing up, I was very much the vocabulary queen, and I love writing (and not so much math).

When I was the marketing director for a company that made physical goods, the pace of change was so much slower. I really like the way that you can evolve technology to meet users’ needs and solve problems much faster than in physical goods.

How would you say your Brandcenter experience supports your journey, or has supported your journey as an entrepreneur?

The Brandcenter was really transformational for me. I don’t think I can say enough about how much it transformed not just my career trajectory, but also how I think about myself. I didn’t think of myself as a creative person when I entered the program. But the school really promoted creative thinking and helped me appreciate how much good design can do for marketing, product development and more. I left there with a much broader definition of intelligence. The Brandcenter really taught me to think differently. And then also collaboration, just learning how to work with people. We did a lot of presentation work and learned how to tell a story and communicate effectively. There are so many ways that the program really impacted where I was headed with my career, and the network has also been incredibly valuable. I wouldn’t have had the confidence to embark on this project without having had the Brandcenter experience.

How do you see the funds from winning the pitch competition supporting Ditto?

I think primarily right now we want to start marketing more broadly, so we’ll be looking at spending a little bit of money on social and pay-per-click just to drive some awareness; not a lot but some perhaps toward referral or affiliate programs.

Our target audience is primarily high-end techie freelancers. We’re focusing first on creative types, so designers, developers and marketers who often do more project-based work with their clients, whether it’s designing logos or a small website. We’ve actually toyed with the idea of trying to present Ditto almost like insurance, playing up the angle that we’re mitigating risk for freelancers — the risk that they won’t be paid, the risk that they’ll be paid late — but we’re also mitigating risk for clients because the payment won’t be released to the freelancer without their approval.

We are hopeful that we’ll be able to start bringing in some revenue pretty soon and then we’ll be able to fund some of those marketing efforts through revenue. We do have some operating expenses on the software side, so it’s helpful to know that we have a little bit of runway with a little more cash in the bank now than we had a week ago.

What was it like to have to pitch during the competition and how did you prepare for it?

I am a complete and total introvert and pitching and presentations have been my least favorite and the hardest part about all of the entrepreneurship stuff. I think it says a lot about how much I care about Ditto that I am willing to get up in front of people to speak because it really is one of my least favorite things in the whole wide world!

I did a lot of preparation, and Claire helped a ton with all of the slides. She was so bummed she couldn’t be there. She likes presenting more than I do. We did a lot of work on the slides and making sure that they told the story that we wanted to tell and in a way that we felt good about, visually. And then I practiced and practiced and practiced. And honestly, I could have done that pitch in my sleep. But my challenge, because I have experienced this before, I can have practiced and practiced but sometimes I get up in front of people, and it’s like my brain just leaves my body and I can’t think. I start to get really nervous and I forget everything I wanted to communicate, and it’s frustrating and embarrassing. I was really relieved that didn’t happen to me this time.

I just have to remind myself to go slowly and try not to panic. And, as I said, we’ve lost a lot of these, so it wasn’t the first time I’ve been up in front of people. You just get better, I guess. I think we’ve pitched at least 10 times, but the number of things that we’ve applied to and not even gotten to the presentation stage, that’s probably closer to 40 … or more.

What’s next for Ditto? Where do you all go from here?

I had been working with a startup in Charlottesville, Virginia, as the chief product officer, but I just gave my notice. I’m going to be leaving that job at the end of this year to really go after Ditto full time. It’s time to turn on the marketing jets.

What we need to do right now is get boots on the ground. We are going to apply to Lighthouse Labs in January, and depending on how that goes, there are other accelerator programs that we could consider applying to but that one feels like the best fit for us right now potentially. We’re just hoping that we will start to acquire users, continue to improve the product and take it one step at a time from there!

2021 pitch competition winners

Alumni entrepreneurs from across the U.S. submitted pitch decks to a selection committee that narrowed the group to five finalists. The finalists had five minutes to pitch their ideas to a panel of judges from the Richmond, Virginia, business community on Nov. 11 at an event sponsored by EY, Covintus and Lighthouse Labs and held at the new Shift Retail Lab.

Elizabeth Heinberg (M.S.’08/B) and Claire Glisson (M.S.’16/B) took first place, winning $2,700 for their project collaboration platform Ditto, which helps make relationships between freelancers and their clients healthier and more productive.

Ayanna McMullen (B.A.’01/H&S; M.P.A.’03/GPA) took home the $1,200 winner prize for The Network Incubator, a creative think tank where entrepreneurs, creatives and professionals connect, create and collaborate to brainstorm business ideas and challenges within dynamic group settings.

Alex Ratti (B.S.’13/En; M.S.’18/En) took home the $950 prize for Light Switch Bio LLC, a preclinical-stage spinoff from the VCU Massey Cancer Center that develops photoactivated chemotherapeutics that minimize the side effects and associated financial costs of conventional chemotherapies by focusing their activity within tumors using a laser device.

Autumn Jones (B.I.S.’20/UC; M.P.I.’21/DVC) was the $700 winner for Simply Autumn LLC, a retail e-commerce business in the beauty, skin care and wellness industry that uses customer-provided data to curate a skin care profile.

Erica Eddins (B.S.’17/WS) won $450 and the title of Fan Favorite for Virtourium, a concept for a virtual tour-streaming service that allows users to easily find tours provided by museums and similar institutions.

Watch the full competition online.

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