Vickie Brennan

U.S. Navy Veteran with over 10 years of Operations and People experience building and managing exceptional teams in Silicon Valley for billion-dollar tech startups including Cruise Automation (GM) (self-driving cars), who was recently listed in the top 3 of the best U.S. companies for career growth, and One Medical Group (healthcare tech) which just had a successful IPO innovating in Primary Care across the US. She is currently one of the Co-Founders at a music tech startup, Chordly, which is developing an app to help people make music easier and is simultaneously the Chief People Officer at CroatiaTech, a Croatian-American technology company in Croatia where she has lived for 2.5 years.

Where did the idea for Chordly come from?

My friend Kyle Robert Bradley had been a self-taught musician for over 10 years and although he could skillfully play all of his favorite songs he was ready to grow beyond that and start making his own original music. He found that making music was hard because it’s formulaic and mathematical. It involved knowledge of music theory, which he definitely didn’t have. He downloaded every app and plugin he could find and watched all the Youtube videos recommended to him but he was still struggling. Without any formal training or study, he was confused and discouraged and he almost gave up on music altogether. That’s when he started thinking there must be an easier way to teach himself and others how to compose music that wouldn’t feel like such a chore.

He then disappeared for 3 years studying ancient music cultures like the Greeks, reading DaVinci’s notebooks, and following countless other music paths. He began formulating everything he needed to develop a way of teaching himself the fundamentals of music. He then decided he wanted to build an app and so he taught himself basic coding and built a prototype.

It was then that he and I were randomly catching up over the phone and he reminded me he had been working on it. A few years before, I had offered him advice on what he would need to build an app from my experiences working in tech. I never imagined he’d actually follow the advice I gave him and put in the effort to learn to code. After seeing what he had built, I decided the least I could do was try to support him so I called up my best friend Daniel Davis who’s a very experienced mobile app developer in San Francisco. We all met online virtually, and after a bit of convincing, we got Daniel to join us, and together we launched Chordly in December 2020 amidst the pandemic.

What does your typical day look like and how do you make it productive?

My typical days are insane these days because I’m currently doing 2 full-time jobs. I’m the Chief People Officer at a Croatian American technology company, CroatiaTech, and simultaneously the Co-Founder of Chordly.

I love my work at CroatiaTech. I love taking care of people and using my operations background to improve the employee experience. I really enjoy getting to implement processes and initiatives to see tangible results in the engagement of our teams. I can’t imagine a day if Chordly becomes successful and I need to think of leaving CroatiaTech because I find working here so fulfilling and I enjoy supporting my CEO and employees.

Luckily because CroatiaTech has been a remote-first company since 2016 the pandemic hasn’t really affected us much and remote work was definitely one of the advantages I saw when I accepted the position. I gain so much time by not needing to commute. I can always fit in doing laundry, cleaning up, or doing the dishes when I have small breaks during the day. We have a very flexible work culture so it allows me to balance my work there with my work at Chordly.

I usually wake up around 7 AM for coffee and checking Twitter, then I get ready around 8 AM while listening to my favorite podcasts about music, tech, or news, and by 9 AM I’m online at work at CroatiaTech. We have a great work/life balance there (and in Europe in general) so at 5 PM I always finish up my day for job #1.

I shut down all work for an hour from 5 PM – 6 PM so I can have dinner with my boyfriend, then around 6 PM I’m starting my day for job #2, at Chordly. Starting in the evening with my Chordly work is good because my co-founders Kyle and Daniel are in New York and San Francisco, respectively, so around that time, they are just starting their workdays.

I typically work on Chordly from 6 PM until around 12 PM during the week but that changes a bit on the weekend. During the week we have a one-hour-long meeting at 9 PM just to touch base and keep each other updated on our progress but on Saturday we have a long 3-hour meeting. On Saturdays, since I don’t need to be up early the next day I’m often awake until 3 or 4 AM working on Chordly projects.

On Sundays, we have a strict “No Work” policy at Chordly. Having been part of many startups before, Daniel and I knew how demanding and consuming a startup can be. It was important to all of us to make balance and rhythm (a Chordly value important to music and life) a priority. We also know how creativity is rejuvenated with rest. So Sunday is always a day off for me and the team to disconnect and enjoy some downtime.

How do you bring ideas to life?

Having been in Operations at tech startups for the last 10 years execution is my specialty. I think it starts with understanding the landscape along with all the pieces, and/or obstacles involved in an idea, problem, project, or initiative.

Once you understand all the pieces you can see where there are opportunities. Then you need to decide which of those opportunities will give you the most impact with the least amount of effort. Those are the ones I go after first.

It’s important to know you’re never going to know everything and don’t let perfect be the enemy of good enough. Just do something! Take action. There are no points for a great idea, done perfectly that launches too late, or not at all. Execution is how you learn quickly, iterate, and win.

I definitely make my co-founders nervous sometimes with the speed with which I work at but I think nothing can replace momentum and once you get in the flow things will just start happening. I try to keep the energy high for my team because energy is really important.

What’s one trend that excites you?

It’s hard to pick just one, I think there are so many exciting things happening right now in the world in spite or, or maybe because of the pandemic. I guess I’m on the AR train. We are definitely looking at it for the future of Chordly.

I really think it’s going to be exciting when it’s as ubiquitous as smartphones are. I think AR will have effects on society that we can’t even conceive of now. More specifically, at Chordly we are waiting for Apple to change the game in AR and when they do we will be ready!

What is one habit of yours that makes you more productive as an entrepreneur?

I’m a big fan of being a lifelong learner and I’m a prolific reader. Being an entrepreneur requires an endless amount of knowledge and doing things for the first time. Of course, now I don’t have as much time to read so integrating podcasts into my life has been a game-changer. When I’m cooking, cleaning, getting ready for my day, and even as I’m falling asleep I always have on podcasts. I’m always learning, hearing new ideas, or finding people to connect with from podcasts. There are so many good ones these days.

What advice would you give your younger self?

I would have told myself to learn as many languages as possible. I think language opens up a new part of your brain and creativity that otherwise remains dormant. Once you learn one language it’s that much easier, usually to learn others.

Now that I live in a foreign country I really appreciate how easily young people can pick up new languages and how much more fully you appreciate different cultures through their language. As an adult, learning a new language is much more difficult. Luckily, I think in the business world, English is widely spoken but it’s always nice to approach others in their native language even if it’s only possible to learn greetings to show you’re making an effort.

Tell us something that’s true that almost nobody agrees with you on.

Resumes are mostly useless and someone needs to innovate on them. I’ve hired so many amazing people who ended up rising through the ranks to be stellar team members or managers whose resumes were passed over by many other recruiters and hiring managers due to punctuation mistakes, time gaps in work, or because they didn’t go to the right college (or any college for that matter).

The only thing a resume reflects is how good someone is at writing resumes and most people are horrible at it; as they should be! I’ll literally spend 5 seconds on a resume but hours phone screening as many candidates as possible for a position so I can really get to know the people behind the piece of paper.

All the old rules for how to evaluate resumes need to go away and we need to find a better way!\

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Guard your time and focus. When you’re an entrepreneur time is everything and always in short supply. I’m always telling people that learning to proactively eliminate things that take away your focus is so important.

Focusing on one thing at a time is the single biggest thing you can do to get more time in your day. Most people lose 30% of their day just from context switching! That’s unbelievable but true, so I’m always looking for ways to minimize distractions and I advise to do the same.

What is one strategy that has helped you grow your business?

We had a great experience with getting our story out on Reddit and gathered over 350 emails for our waitlist from a single post. Reddit is notorious for smelling a sales pitch and they won’t engage with brands that aren’t authentic. We told them our personal story about why we were building Chordly and that we understood what they struggle with as music creators because we did too. We are still getting upvotes today from that post and we have answered every single comment and question, being sure to thank each one for their interest and support. Letting customers know that you’re real people first and a business second goes a long way.

What is one failure you had as an entrepreneur, and how did you overcome it?

One major failure I had as an entrepreneur was at the beginning of working on Chordly I was so excited to get going and I posted on Reddit about our app because we were hoping to get a couple of people to test it. I couldn’t believe it as hundreds of people started going to our website to submit their information to our waitlist.

I couldn’t wait to tell my co-founders and I was completely caught off guard when Daniel, my technical co-founder, got really stressed out and upset with me because now he was under pressure to release the app quicker. I had been so caught up with the success I had in my role that I didn’t stop to think about when and how to tell my team, or to consider what the implications were then for them.

That was a really good lesson to learn early on about considering my team members’ feelings and their perspectives. Also, we had a plan for what to do if we couldn’t get users but we didn’t have a plan in place for getting hundreds of users. Since that time we always plan for both success and failures.

What is one business idea that you’re willing to give away to our readers?

I think someone should form a community for entrepreneurs’ spouses, partners, and family to go for support. Especially in the startup world that I’m in it’s often those around us who sacrifice the most. They get dragged along on all the highs and lows of entrepreneurship but have little control over the course of things that greatly affect their lives too.

They are the people behind the scenes that make it possible for us to do what we do and I think only someone who’s been through it can understand what they go through supporting us, as we chase our dreams. If there are thousands of entrepreneurs then there are at least that many people supporting us and it’s a very underserved community. Actually, I’d say it’s not served or thought of at all.

What is the best $100 you recently spent? What and why?

I recently just got tickets to the InMusic Festival being held in Zagreb, Croatia this year. It actually only costs 67 euro ($80) for a 3-day ticket. It was supposed to happen last year but COVID prevented it. I’m really excited to hopefully, finally be able to go to a concert again and the lineup is so great; The Killers, The Deftones, Beck, and The Lumineers are all playing. As someone who loves live music and has a company in music/tech this is something I’m really looking forward to, especially since it’s in my adopted country and Croatia isn’t exactly known as a typical stop for such major musicians.

What is one piece of software or a web service that helps you be productive?

At Chordly we love Notion. Notion is web software that incorporates components such as notes, databases, kanban boards, wikis, calendars, and reminders together, similar to Google Drive but more powerful and designed better. We use it for everything and it helps us collaborate, plus it’s fun to use. We spend way too much time deciding which emoji should accompany each page.

What is the one book that you recommend our community should read and why?

“The Rise and Fall of American Technology” by Lyn G. Gref. The author was my Co-Founder Daniel’s office mate when he worked at JPL (NASA Jet Propulsion Laboratories) and it’s pretty much required reading at Chordly. It’s a really interesting view of the technology lifecycle. The book describes “how technology gets developed, America’s rise to global dominance in technology and salutes its golden age with an overview of many breakthroughs that improved our standard of living and lifted every boat.”

What is your favorite quote?

“Don’t get high on your own supply.” I think the point of this quote can be useful in so many ways but basically, it’s a warning not to lose focus. Not to let yourself be distracted. Remember what you’re doing and never lose sight of that, or suffer the consequences.

Also, don’t get too high on your own opinions. Be open to new viewpoints and new opinions. Generally, always keep the bigger picture in mind. That will keep you on track when things get hard or when you don’t know what your priorities should be.

It’s also a pretty unconventional piece of business advice but some of the best business people I’ve known have been the people that hustle because it’s a matter of survival. I like being unexpected and a bit rebellious so this piece of advice accomplishes that too.

Key Learnings:

• Focus and execution are irreplaceable to entrepreneurs to maximize time, which is always in short supply. Combine them with downtime to recharge creativity and you have a long-term strategy for a successful business.
• Incorporating podcasts into your routine enables entrepreneurs to multitask in a productive way by learning while accomplishing daily chores that need to be done, maximizing your time.
• Resumes are only good at determining how well someone writes resumes and actually have little bearing on how someone will actually perform in real life. Phone screen as many candidates as possible and you’ll find some hidden gems.
• Thank those in your life who make it possible for you to be an entrepreneur. Find ways to offer support to spouses, partners, and your family that sacrifice so you can chase your dreams. Make sure to take time to let them know you appreciate them and that they are a priority too.