Female Founders: Chelsey Roney of Proxi On The Five Things You Need To Thrive and Succeed as a Woman Founder
An Interview With Candice Georgiadis
Learn how to communicate the progress you’re making in your business/successes in a succinct way. People want the ‘TLDR’ and will be able to help you much faster once you’re able to condense your thoughts. I used to be indirect in my communications. I worked on my first business with my husband. He once told me he had no idea what contributions I was making because I was being too indirect with my value-add. This taught me that I need to say what I mean without hesitation.
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Chelsey Roney.
Chelsey Roney brings her business-building and strategy experience to Proxi, where she serves as COO and leads a team of 5, growing the business through sales and marketing. After graduating from Texas A&M, Chelsey joined Boeing where she worked in financial planning and analysis and Microsoft where she worked in a demand center that focused on B2B omnichannel marketing. She grew and sold two businesses: a SaaS business in the University space, and a local services business.
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?
Sure! Looking back, there were signs that I was going to be a female founder very early in my life. I started my first operation at around age 5. I set up a restaurant in my grandmother’s kitchen complete with menus, prices, and table settings. I took orders, ‘cooked’ and of course collected a little extra change. As a child, I went on to sell flower bouquets to neighbors, start a very profitable pet watching business, a very busy private swim lesson company, and in high school repackaged my notes for others. I went on to start my first SAAS company at age 21 (I sold it in my late 20’s) and bought my second company at 30. Meanwhile, I went to Texas A&M University to study Finance, which is what I thought and was told would lead to a very steady career. I subsequently worked at Boeing, earned an MBA and then worked at Microsoft. I very much enjoyed my time at both companies and learned a lot while I was there but looking back at my passions and how I spent my free time, I was always called to spend my time as a founder.
Can you share the most interesting story that happened to you since you began leading your company?
The most interesting thing happens to us daily — people and businesses find and use Proxi for use cases that we never would’ve imagined! Proxi is a free technology anyone can use to create and share interactive, branded maps. We have had thousands of maps made on Proxi. Many of our highlighted use cases are ones customers have come up with. Individuals have created such varied maps as guides for their out-of-town wedding guests to spots that marathon attendees can cheer on their loved ones. Businesses and non-profits have mapped everything from volunteer events to the stores that carry their inventory. One of our most unexpected but exciting use cases was Seattle Restaurant Week creating a map to show where all participating restaurants were located! There were several hundred thousand views by the end of spring 2022 restaurant week.
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?
I’ll tell you the (now) funniest mistake I’ve ever made in my career. When I was at Microsoft, I sent emails to customers who were interested in the Surface line of products. Once, on accident, I sent a completely blank email to several hundred thousand people. I still feel horrible about it, but now I laugh about it too. It had the highest open rate of any email sent around that time. If only I had included a single link to a product in that email! I’ve learned to have an outbox delay set and have extra eyes on any outward communication that goes to a large number of people. You can never do enough double checking!
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?
I am most grateful towards my parents. They consistently told me I was/am an intelligent, strong human who could do whatever I set my mind to. They spoke this into me so often, that I really believed it and still do. To this day, my parents are invested in whatever I am passionate about and devoted to. It gave me the confidence to go after big ideas at a young age and think ‘Why not?’ to things that seem out of range.
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?
I absolutely think it’s the support she has around her. Women need other people to 1) pour education and encouragement into them and 2) physically support her dedication to her company. If you are a founder, you will have less time for household activities of which women typically bear the load. The people around a woman can make or break her dream of being a founder. In my opinion, women should verbalize what they need from the people closest to her in order to start a company and people should help her remove as many barriers to entry as possible.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
Two things. 1) It would be very helpful for governments to provide (limited time) stipends to live on if you are a woman (or anyone) starting a business. Starting a business is oftentimes saved for those who have the financial capacity to reduce their earnings for several months or even years. To open founding a company to more people, there must be financial support. 2) This is probably top of mind because I happen to be a mother of two young kids, but as a society, and especially during COVID, childcare for working parents (especially for moms) has been an incredible burden. Childcare is enormously expensive, and therefore prohibitive to start a business and have children at the same time. We need to find a way to subsidize this expense and make it very reliable (you can’t make much progress when your child is at home every other week due to closures!).
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
Women can think about many aspects of a situation at once and organize the workstreams for each because a lot of the time they are doing this outside the workplace and have been doing so for their whole lives (not saying this is the way things ‘should’ be but it does so happen that it is the way things are a lot of the time). This is a highly applicable skill as a leader of a business because there are lots of facets to work through and many things/people to care about.
What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?
I think the biggest misconception about founders from the public is that they always know what to do next. This couldn’t be farther from the truth! Most founders do not know what the exact next step should be, but they make educated guesses based on research or experience to move forward. People ask me often, “How did you know to do that?” I research, plan, and take moderate risks. I act confident about my decisions and then learn from the outcomes.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
No, I do not think everyone is cut out to be a founder. I think everyone has the *ability* to learn how to be a founder, but you must really want the career path because it is grueling and impacts all aspects of your life. If there’s even a 5% doubt on if founding a company is a good idea, then it may not be for you. Being a founder means figuring things out with the resources and connections you have, much of the time on your own. If you feel like you need to ask someone the next step for a new topic you are learning, it will make life as a founder difficult, because you must learn to move fast on you own. Being a founder means working toward something against doubt and odds. It means pushing through on days when you think things might fall apart. But pushing through is where the magic happens! Consistency is key.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- You’ll need to learn how to bounce back from adverse situations quickly. A growth mindset is key to development. When you hit an uncomfortable situation, acknowledge the negative feelings, but then turn them into learnings. If you can reframe thoughts about how you wish you could change something to ‘I learned this for next time…”, you’ll start to see yourself grow over time. I’d recommend keeping a list of your lessons learned! One day, it will be fun to look back at. When I was early in my career at Boeing, I was surrounded by very experienced professionals. If I made a mistake, I used to get incredibly embarrassed. It led to me keeping my opinions to myself and making myself small. When I got to Microsoft, ‘growth mindset’ was talked about often. I began transforming any negative interaction or feeling into a learning. It truly transformed the way I conduct myself in the workplace and how I interact with my employees today.
- Train your brain to speak positively about yourself to yourself. Turn every thought about imposter syndrome into something you like about yourself. Eventually, you’ll believe the positive thoughts more than the negative thoughts. Like many people, I have struggled with self-doubt. About 7 years ago, I read somewhere that every time you have a negative thought about your abilities you should turn it into a positive thought about yourself and repeat it over and over again. Now, in situations where I feel I’m out of my league (especially as I learn more about growing a rapidly expanding venture backed company), I pump myself up with positive thoughts when I feel nervous. But that was a learned behavior!
- Always speak with confidence. Remove any doubt, extra words and “I’m sorry’ s” from your vocabulary and speak with conviction. You’ll notice a huge difference in how people respond to you. It took a long time for me to realize being apologetic about myself or my hopes/dreams was not doing me any favors. I edit my communications to remove language that might convey anything but confidence and conviction. These written edits also help me when I am verbalizing.
- Be the most prepared person in the room. Come with agenda items, good questions, and thoughtful insights about what others are staying. I sometimes ask myself, “What can I do to have the most informed opinion in the room?” The extra prep might take 10–15 minutes per meeting/interaction, but it will help you get so much more out of your scheduled time with others as well as improve your image. When I was at Boeing, one of my mentors gave me this advice. I couldn’t figure out why I wasn’t able to participate meaningfully in meetings. He told me that I need to come to the meeting as the most prepared person in the room. Putting this into practice radically changed people’s perceptions of the value I create. Sometimes now, I don’t have the time to prep for certain meetings, and I notice the impact. Coming prepared is the biggest factor in future success, in my opinion.
- Learn how to communicate the progress you’re making in your business/successes in a succinct way. People want the ‘TLDR’ and will be able to help you much faster once you’re able to condense your thoughts. I used to be indirect in my communications. I worked on my first business with my husband. He once told me he had no idea what contributions I was making because I was being too indirect with my value-add. This taught me that I need to say what I mean without hesitation.
How have you used your success to make the world a better place?
I have used my ‘success’ to employ people both at Proxi and at my prior two companies. I think job creation is one of the best ways to support your community. However, it’s not just enough to be an employer. I work hard to create a positive environment for my employees in which they never dread coming into work. It’s my hope that happily and gainfully employed citizens contribute to their communities in positive ways.
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.
I would like to teach people how to find a job that aligns with their passions. This might mean helping people feel confident enough to make a career change or learn ways to monetize what they enjoy thinking about and doing in their free time. I strongly believe there’s a way to at least have some portion of your job align directly to your biggest passion. Personally, I am so much happier when I concentrate on what I love every day. For me, I am most engaged and gratified when I spend my days figuring out the pieces to put together a ‘successful’ company. If everyone were able to feel as happy as I am to wake up in the morning, I think the world would be a better place for everyone.
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.
I’d love to have a private lunch with Sarah Blakely. She’s got incredible work ethic, treats her employees well and sticks to the vision!
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Female Founders: Chelsey Roney of Proxi On The Five Things You Need To Thrive and Succeed as a… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.