Reading: Becoming a Tech Founder After 50

It’s not often someone’s morning commute is so inspiring that it sparks an entire reinvention. But that’s exactly what happened for Amy Giddon, the cofounder and CEO of Daily Haloha. Giddon spent the first part of her career consulting and in executive roles at financial services companies. She’d made it to president of one of those financial companies, but then a #MeToo moment set her on a path to creating leadership forums for women. One day, while she was rushing through Union Square Station in New York, the idea for an app to connect us more deeply to others was born. 

“It is designed to uplift each of us, and all of us, and to be an oasis from the divisive digital din that surrounds us these days,” Giddon says. “Envisioning and then building something from scratch, especially something I believe will be healing in the world, is an incredible feeling.”

Giddon never expected to be a reinventor, especially not as a tech founder over 50. Here, she shares what’s made her journey hard, what has worked best, and how she stays motivated and keeps doubt from taking over.

TheCovey: What was your reinvention path?
Amy Giddon: I started my career as an associate consultant at Bain & Company, a global management consulting firm and currently (it’s too early to say “I ended up as”!) I’m an entrepreneur. I’m the cofounder and CEO of the mobile app Daily Haloha, an app to connect us more deeply to ourselves and others through simultaneous reflection on a daily thought-provoking fill-in-the-blank question. We hope to restore a bit of empathy and affection for humanity. 

This, however, was no straight path. I spent many, many years hopscotching between consulting, both for large firms and my own consultancy, and executive roles in financial services companies. Before I started this reinvention, I was the president of RushCard, a private-equity backed prepaid debit business (since acquired by Green Dot).

TheCovey: Why did you reinvent?
Amy Giddon: My job at RushCard was both the best role I’ve ever had, and the most distressing. The RushCard customer was largely disenfranchised and left behind by mainstream banking. Our products and services enabled our customers to transact their financial life securely and with dignity. After working at the most affluent end of the payments market at American Express, this work felt meaningful. I had also expanded my role to include Product Development. I loved waking up every day imagining the products and features we could create to make our customers’ lives just a little bit easier. And because RushCard was considerably smaller and more entrepreneurial than my past employers, there was a scrappy sense of possibility and “just do it.” My career until this point had mostly been about bringing insight, structure, and planning to companies. And now I got to imagine and create and build. It was a new and exhilarating feeling.

But then I had a different new experience — I was sexually harassed, although I didn’t use those words at the time. I was propositioned by someone more senior and my rejection caused so much tension in our working relationship I eventually left my job and the company. I was angry and stunned: angry that others’ bad behavior forced me to leave a job I otherwise loved, and stunned about what had happened. I was the president of the company and almost 50 years old, dammit! I kept rehashing what happened, asking myself what I could have done differently. I finally realized that I had resisted calling it what it was — sexual harassment — in a misguided attempt to maintain my dignity. In my mind, being harassed made me lesser, diminished, less powerful. It felt like giving something up to call it what it was. I’ve come a long way in my understanding of these power dynamics.

When I stopped rehashing, I started reinventing. I had always enjoyed mentoring the younger women in my companies, and sharing the lessons I learned as I navigated my career. And boy did I have some lessons to share. So I pivoted completely from running businesses to developing leadership programs for other women leaders as major Reinvention #1. I worked at the Athena Center for Leadership Studies at Barnard College and Columbia University, working with companies committed to seeing more of their women leaders achieve positions of influence. Through this work, I not only supported other women in the pursuit of their ambitions, but I was able to decode my own career experiences. This was an important part of my process of getting back in touch with what mattered to me most, regaining my footing as a leader, and reigniting a sense of possibility. This first reinvention opened up the idea that reinvention is not only possible but can move me closer to what I care about most. It paved the way to an even bigger reinvention later.

TheCovey: And that “bigger reinvention” was Daily Haloha?
Amy Giddon: It was! Three years ago, while commuting daily through the Union Square subway station in NYC for a consulting assignment, I experienced a collaborative sticky-note art project called Subway Therapy. New Yorkers were reeling from the divisive and dehumanizing presidential election, nerves were frayed and relationships were strained. While rushing for their subway, these New Yorkers caught a glimpse of a colorful sticky-note display blossoming across the walls of the subway station. I saw how these commuters were drawn to the wall and how by reading just a few of the notes, they instantly understood the intention of the project: to provide affirmation and unity in the wake of the polarizing election. They looked around for a way to participate and beelined for one of the stacks of blank sticky notes. They paused, and thoughtfully wrote out their own note to contribute. They added their note to the wall and invariably took a photo to post and share. Often they would then take a step back and take a picture of a bigger expanse of the wall with their own note in the middle of it all — as if to say “here I am, part of something bigger. I’m here too.”

I was riveted by how the project captivated and uplifted the people rushing by, who stopped to contribute, culminating in 50,000 bits of humanity. I studied other collaborative art and storytelling projects around the world and saw how, in just a few short moments, they consistently created a sense of connection among strangers. I was struck by how they were the opposite of social media, which in many ways has failed in its promise of connection, instead creating a home for increased tribalism, outrage, and social anxiety. I imagined how the qualities of participatory art — anonymity, freedom from judgment, and absence of social status — could be recreated digitally. In one feverish night I wrote down the first iteration of a whole new concept — a mobile app for social well-being that uplifts us and connects us to our shared humanity.  

The Daily Haloha mobile app was born. Daily Haloha serves up a two-minute flow of reflection and connection kicked off by a single, thought-provoking question to the world each day. It works like this:

1. Me: Reflection. Reflect on the day’s question. Write a response and give it a mood color.  It’s all anonymous and judgment-free. You can be authentic, vulnerable even.
2. Me and You: Reciprocity. Send off your Haloha to be delivered randomly and anonymously to one other person – and receive one back from someone else. Surprise!
3. All of Us: Perspective. View the collection of the day’s responses. Be moved, amused, and inspired by anonymous others united in reflection on the day’s question.

It is also a reflection, an embodiment actually, of my personal values: that everyone matters and that what we share as humans outweighs what divides us, if we can just remember it! And that feels amazing. 

TheCovey: Does Daily Haloha pay the bills?
Amy Giddon: Not yet!  We are just getting going, but we have a revenue-generating business model in mind for the app when we have proven its value to users and are ready to scale and grow. In the meantime, I am not taking a salary and we are pre-revenue, so it is a fragile financial time for me.

TheCovey: What kind of financial planning did you do?
Amy Giddon: At first, I was self-funding the business along with my cofounder, who joined me along the way. When that was no longer feasible, I raised money by doing a friends and family fundraiser via a convertible note. I have eight investors who have contributed $275k. I feel a great gratitude toward my investors who made a financial bet on us so early in the life of the company. I also feel an incredible responsibility to be the best steward of their investment I can be and to hopefully give them a great return on their investment.

TheCovey: What was the biggest surprise about reinventing?
Amy Giddon: I’ve had so many surprises about what it takes to start a company, develop and market an app. But the biggest surprise of all is how I would feel as a founder of a company. I had not had the aspiration to be an entrepreneur and have always felt comfortable working within corporate structures and being in service to other businesspeople as a consultant. I quite enjoyed having bosses and clients to whom I needed to deliver results and recommendations and I enjoyed even more the positive feedback and appreciation I would receive in return. I didn’t realize until I was my own boss how much I missed getting that feedback. While it feels amazing to work toward a vision that is wholly my own, I’ve really had to learn to be happy with my own sense of accomplishment rather than external validation. I wasn’t even aware of how hooked I was on appreciation and validation until I had some empty-feeling successes and could pinpoint why I felt deflated. I’m learning to be my own cheerleader. 

TheCovey: Did you meet any resistance from family, friends or coworkers?
Amy Giddon: I didn’t meet any overt resistance from those close to me, but it took a while for everyone to realize how serious I was about building a business, and how much I was willing to sacrifice to make it happen. When I described my vision for an app to rekindle empathy and to be an antidote to social media, my friends and family thought it was admirable and probably a sweet and idealistic idea. They didn’t understand the determination and ferocity with which I would pursue my plan. I dealt with this by buckling down and doing the work, and finding people who cared about the things that I did. I figured the end result would speak for itself.

TheCovey: What have you learned about being a reinventor? Would you do it again?
Amy Giddon: I have learned so much about myself by being a reinventor and specifically from putting myself so far outside my comfort zone. All along the way I would stop and ask myself: if we fail, will I regret having done this? I am still saying “no” to that question. I have learned things about myself that I wouldn’t have had the opportunity to uncover otherwise. And because my reinvention involves working in complete alignment with what I care about most, it has put me on a path with incredible people I never would have met otherwise. But it’s been really hard and sometimes scary. If not for such a deep belief in our mission and purpose, I may have let doubt take over. I may yet experience a series of pivots in pursuit of my intention, but if I can have the impact I want to have in the world, I can tolerate the twists and turns.

TheCovey: What do you think has been the one secret to your success as a reinventor?
Amy Giddon: Probably not thinking about my reinvention as a reinvention but rather an opportunity to be more of who I already was and have always been. My reinvention has entailed taking some bold steps to express what I have always cared about and to be of service to others who care about the same thing. This expression happens to be a mobile app, which is a big departure from my past work, but my reinvention brought me home to myself. This has been important to my success, because people feel my deep commitment to what I’m doing and I get reenergized every time I talk about my venture. Also, it enables me to connect my career dots for people and describe the through line so people don’t see my current venture as a wild and new idea but rather as the next step in my evolution. This makes it easier for people that have been in my network for quite a while to come along on my ride and support me and Daily Haloha.

TheCovey: What are two unexpected tips you can give our readers?
Amy Giddon:

1. Don’t mistake the people who love you for the people who will love your reinvention. It may be hard for some people to come along for the ride. They may be nervous for you. Or stuck in an old idea of you. It’s OK, they still love you and you will find a whole new tribe who love the reinvented you.
2. Follow your energy. Take note of when you’re in flow and the time just flies. Also take note of what you keep putting off and what drains you.  Reinvention is the opportunity to become reenergized. What else would be the point? 

TheCovey: What would you warn others never to do?
Amy Giddon: I don’t really believe in absolutes, but I will caution reinventors when it comes to who to listen to and what “advice” to act on. It can be hard to know what to do next or to make decisions when reinvention brings you into a new sphere of work. So naturally, you will want to seek advice and counsel from your network and from experts. And don’t confuse the two. It’s natural to turn to your network for advice but do they really have expertise in the subject area? Are they your target market? It’s wise to cast a wide net and get multiple points of view when making a decision in an uncharted subject. Everyone has an opinion but they’re not all equal!

TheCovey: Anything we didn’t ask about but you need to tell us here?
Amy Giddon: We’re super-early in our journey and looking for feedback, collaborators, and supporters.  Download our free app, take it for a spin, and let’s talk! www.dailyhaloha.com