On Second Thought Founder Maci Peterson Philitas Harnesses The Power Of ‘Undo’ To Take Back Sent Messages

Ebony Grimsley-Vaz
Written by Ebony Grimsley-Vaz
Take back sent messages
After a mistake with an ex-boyfriend, Maci Peterson Philitas searched for an app that would let her take back sent messages. Not finding one, she made one. Peterson Philitas is the founder and CEO of On Second Thought. Photo by Keith Munyan

We all depend on tools to try and catch our mistakes but there are still things machine learning cannot fix. Like that email you shouldn’t have sent to a colleague or the $20 you sent to the wrong person instead of reimbursing your friend for picking up the lunch tab.

Maci Peterson Philitas, founder and CEO of On Second Thought, wants to help you with that.

After making one of those mistakes with an ex-boyfriend, Peterson searched for an app that would let her take back sent messages. When she couldn’t find one, she decided to create it.

Like about 71 percent of Americans, I needed the ability to take back messages before the recipient receives them.

Maci Peterson Philitas, founder and CEO of On Second Thought

What started as a business-to-consumer mobile text messaging app quickly spread to 190 countries and gained over 125,000 downloads, Peterson Philitas said. Her business has since evolved into a business-to-business tech solution for large companies.

“I don’t know about you but autocorrect has a vendetta against me,” Peterson Philitas told Moguldom. “I started On Second Thought so I could undo messages before they got to the other person.”

Investors bought into it. Backed by $1 million-plus in capital, On Second Thought has grown its product offerings.

Peterson Philitas spoke with Moguldom about her thoughts on pitch competitions, overcoming challenges in launching a startup and what’s next for On Second Thought.

Moguldom: Why did you start On Second Thought?

Maci Peterson Philitas: I don’t know about you but autocorrect has a vendetta against me. I started On Second Thought so I could undo messages before they got to the other person. Like about 71 percent of Americans, I needed the ability to take back messages before the recipient receives them.

Moguldom: Your background is in public relations. Did you ever see yourself becoming a Black tech founder?

Maci Peterson Philitas: I didn’t set out to become a Black tech founder. I feel like tech found me. My background is in public relations and advertising, but I have always been an entrepreneur at heart and in profession. I started my first company while I was in college. It was one of the first digital magazines for women of the African diaspora. That’s why I love Moguldom — because it feels like my roots. I then went on to The Root where I ran their digital marketing for three years. From there I went to Marriott where my job was to relaunch their mobile game.

On Second Thought wasn’t the first time I ever worked in technology, but I didn’t set out to work in technology. I set out to solve a problem that was taking back text messages. The solution just happened to be technology.

take back sent messages
Maci Peterson Philitas, founder and CEO of On Second Thought. Photo: Telecom Council

Moguldom: Without having a developer background, how did you go about building the team to create your products?

Maci Peterson Philitas: I don’t have a tech background but I have a great network. I always had a really incredible network and community of people I knew I could trust and are really great at what they do. When I came up with the idea for On Second Thought, I didn’t know anything about technology or startups, but at the same time, I did. While I was living in D.C., I constantly found myself at tech meetups. My friends were starting to get involved in the startup space and I would join them for happy hours. When I came up with the idea for On Second Thought, I’d already been plugged into the community and I already had those relationships. I knew exactly who to call to figure things out.

I would recommend only pitching when there is a cash prize because you’re investing your time away from your company to compete. Keep in mind the judges can help provide validation, but they’re not always right. If you feel in your gut you should keep going, do so.

Maci Peterson Philitas, founder and CEO of On Second Thought

While I am not a product person and I do not have a technical background, one of my good friends from college does and he is my co-founder. I could not only trust him, which I think is the most important quality for a co-founder, but I also knew he would know how to build the product.

Moguldom: You have won and participated in pitch competitions. Is it worth being in them as a startup?

Maci Peterson Philitas: One big positive with pitch competitions is you get immediate validation. When I pitched at the competition at SXSW, On Second Thought was just an idea. I didn’t even know if it was viable. By winning that competition, it validated that not only was it a good idea, but it could also be a viable business.

As we did more pitch competitions, they were beneficial for a couple of reasons. One, it helped to get non-dilutive capital in the door, meaning the money was basically grants because we didn’t have to give up equity for them. The other thing that was helpful with a couple of the competitions is we were in a lurch from a capital standpoint and those competitions provided us with the infusion of capital we needed precisely when we needed it.

In terms of my advice to other entrepreneurs on pitch competitions, unless it is a great, great opportunity, I say don’t pitch for free. I would recommend only pitching when there is a cash prize because you’re investing your time away from your company to compete. Also, keep in mind the judges can help provide validation, but they’re not always right. Just because you don’t win, doesn’t mean you’re not onto something. If you feel in your gut you should keep going, I highly recommend you do so.

Moguldom: How much have you raised in capital thus far?  

Maci Peterson Philitas: So far, we have raised, a little over $1 million. When you include prize money, it is over $1.1 million in capital.

Moguldom: With the infusion of capital, you’ve gone beyond just looking at mobile text messaging. What does On Second Thought offer today?

Maci Peterson Philitas: We pivoted from being B-to-C to B-to-B. When we launched our app, it was a proof of concept. We quickly spread to 190 countries and gained over 125,000 downloads. It was really cool hearing from our users around the world and how much they loved our technology.

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We would be asked if we could help them with the platforms they use every day. For example, we heard from users in Kenya who wanted to know if they sent a payment to the wrong person is it possible to get it back. Or, they would say, “We love your technology but it doesn’t work in email, Twitter or WhatsApp.”

Basically, they were asking us to help them fix the mistakes they were making every day. One of the largest telecom companies in the U.S. approached us about licensing our technology. And with that, my co-founder and I realized that through licensing, we could empower people to fix their mistakes on the platforms they were using every day whether they were sending a payment or a message. And so now we license our technology in the form of an SDK. Our customers’ users can undo messages with OST Undo, without needing to download any additional software. Our other product is called OST Money. It works with peer-to-peer payment platforms so our customers’ users can undo payments before they get to the wrong person.

We have been issued our first two patents, and we’re currently working on our third. Raising over a $1 million in financing and being one of a couple of thousand Black women to have done so is a win.

Maci Peterson Philitas, founder and CEO of On Second Thought

Moguldom: You are approaching six years in business. Most small businesses don’t make it past three years. How have you overcome the challenges and what have been some of wins?

Maci Peterson Philitas: Number one is faith. Faith in myself and faith in God. The other thing is perseverance. No matter how many no’s I’ve received — there have been hundreds of them — we kept going. Humility has been another one. Understanding that I don’t know everything but surrounding myself with people who do has been tremendous. I’ve known exactly who to call, whether our advisors or investors or people who I respect in the field. They’ve helped us think through some of the challenges we’ve had and provided solutions on where we should go.

I’ve also learned a lot of people will offer advice, but it doesn’t mean it’s right. Sometimes it’s really bad advice. It’s important to have wisdom and to trust your gut. Our relationships have been helpful too. Being in meetings with the CEOs of Fortune 500 companies or entering into agreements with some of the world’s largest corporations has been really, really incredible. I would say I’ve experienced more at 32 than most people do in their entire life and that’s a blessing.

take back sent messages
Maci Peterson Philitas, founder and CEO of On Second Thought, receives a check from Women Who Tech Startup Challenge.

We have been issued our first two patents, and we’re currently working on our third. Raising over a $1 million in financing and being one of a couple of thousand Black women to have done so is a win. I’m really grateful for our team. It is small, but we have spread to pretty much every country on the planet. It is very humbling to see we’ve helped people in such a meaningful way.

Moguldom: You were just honored by your high school. What would you say to the young Black girl or woman who wants to become an entrepreneur?

Maci Peterson Philitas: If you have something in mind that you know you want to do, just do it. Technology has broken down so many barriers that you should just do it.

Moguldom: What do the next five years look like for On Second Thought?

Maci Peterson Philitas: It’s hard to say because with startups everything changes. I believe our technology will be ubiquitous. Everyone will have the ability to fix your mistakes on all the platforms you use every day. We want you to have access to our technology everywhere, whether it’s on your phone, your desktop or your tablet.