How They Did It: Leah from

I'm so pleased to feature my friend, Leah from I absolutely love her blog and free resources because there's no fluff. Just usable advice and actionable tips on how to take your side hustle game and personal brand to the next level. She's helped me a ton in both these regards. Leah is an amazing motivator, all around #bossbabe and I'm excited for you to learn more about her journey today.

Without further ado, let's dive right in!

Tell me a little about yourself and background.

First of all, thank you, Kim, for inviting me to be a part of this series! The title, “How They Did It”, throws me off at first because I can’t help but think, “did what?!” We really are our own worst critics :)

My name is Leah and I’m from a small town in Colorado but moved to New York City about 7 years ago to attend NYU. I studied international and sustainable development, which I’m extremely passionate about and have carried with me to my day job, which works to improve and innovate the field of philanthropy. I love my job and every morning I walk to work in slight disbelief that I get to do it every day.     

Please tell me about your WEBSITE and mission.

My website,, is an online resource for millennials who want to get ahead during their young professional years, specifically by focusing on side hustling and personal branding. This work is inspired by the advantages and opportunities our generation has to make a name for ourselves at a young age, make money on the side with several streams of income, and essentially use the digital age to redefine our professional and financial opportunities. is the bridge between your personal, professional and financial goals and the opportunities out there that will allow you to achieve them.

What inspired you to start this journey to create your own business?

Though I love my job now, it wasn’t always this way. About a year ago, I was in a tough spot... I had been accepted into law school, a lifelong goal of mine, but was having a change of heart given the cost of law school and, honestly, the lack of creativity that came with the field (first world problems). My heart was telling me not to go to law school but my head was telling me I absolutely should, because if I didn’t go, I had no idea what else I was going to do! I had put a lot of eggs in that basket, even working as a paralegal since undergrad.

When I was debating, l took a leap of faith and declined my acceptances and even quit my job to travel alone for a while. This inspired me to create, to provide tools and resources for all millennials to take more risks, and to me that means creating multiple sources of income, branding yourself, and networking strategically. Working on these areas helped to build security, which helps you take risks. It’s a dream come true to bring this community of millennials together - empowering each other to be more free.

What's been the hardest part of your journey as an entrepreneur?

The hardest moment so far was receiving my first mean comment. I couldn’t believe how much it affected me, but it did! I couldn’t shake it for weeks. We all know that the internet is the easiest place to be mean; as an anonymous and distant bully. Nonetheless, I’m sensitive by nature and take criticism to heart. Being an entrepreneur means hearing “no” 9/10 times, but that 1/10 “yes”, the “yes” to something you built completely on your own, makes it worth it. Still, I’m working on thickening my skin.

What has been the most rewarding aspect?

Hearing that I’ve helped or inspired anyone to take a risk that they were on the fence about.

I’ve also been surprised at how much I’ve learned about myself, which is why I think everyone should blog. It was thanks to my blog that I quit my old job and declined law school, because I was blogging about innovation and creativity as means to a profession. I realized I wasn’t taking my own advice!

Name 3 strategies or tools that are critical to your success as an entrepreneur.

  1. BoardBooster. This was one of the first investments I made in my blog, when it was in its infancy and far before I was making any money of it, and it was the smartest thing I could’ve done. BoardBooster is what I attribute nearly all my initial growth to. I pay $15/month on it and am happy to do so every month because of how much easier it makes my life and how much traffic it drives to my site.
  2. Cold E-mailing. At events for young professionals, I hear often that cold emailing will never work and that you have to offer something beneficial to the person you’re emailing in order for them to email you back. I have not found this to be the case in my experience. Perhaps this is because entrepreneurs that I email are more sympathetic to the classic cold email than other types of professionals since they, too, were in my position, but cold emailing has led me to more connections and relationships than I could’ve dreamed of. This has included Skyping with Ann Shoket, former Editor-in-chief of 17 Magazine, having a pizza date with Melyssa Griffin, one of the most amazing online entrepreneurs out there, and interviewing Nicole Lapin, my ultimate career role model, for my blog.

    Related: I wrote an article on writing cold emails here.
  3. My Side Hustler Planner. This might seem silly to some, but this was the very first thing I made to give out on my blog and I still use the concept every single day. It’s helped me manage my time SO much better, and when you’re hustling around your 9-5 job, time management will make or break you. The most common concern I hear from young professionals wanting to start a side hustle is that they don’t have time, but the truth is we’re all busy, and this planner helped me find where in my schedule I could more efficient and free up time I was wasting on things that weren’t helping me overall.  

    Related: Get my side hustler planner here.

What are your goals for the remainder of the year?

Mostly to help as many millennials feel more in control of their careers and finances as possible. I’ve learned so much in the last year between traveling alone, quitting my job, months of unemployment, and eventually landing the job of my dreams and I am determined to help other women feel comfortable taking risks, too. I’m by no means a personal branding or passive income expert, far from it, but I hope that by adding the exact way some of the things I write about have helped my life will be engaging to others.

What book are you currently reading?

Boss Bitch by Nicole Lapin, which launches in stores and online in 2 weeks! She’s one of my ultimate career role models and her book gives excellent tips for women taking control of their careers- no matter what career they’re in or what their career goals are. And, she’s so funny. Pick up your copy!

Any advice to the readers who may be hoping to take a leap of faith in their own careers?

Taking risks and bravery are muscles; they need to be exercised. My father taught my sisters and I growing up that the younger you take risks and believe in yourself, the better you get at it. This will help you take bigger and greater risks down the road and as a result, help you lead a more fulfilling and exciting life. My biggest piece of advice is to trust yourself and know that you can achieve your dreams, even if you’re not exactly sure how.  

Thank you so much for having me, Kim!


If you're not already subscribed to Leah's website please head on over to and check it out. You may also find her on Twitter @U20Something and on Instagram @urban20something. Thank you so much for being a part of this series, Leah!


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Do you have an inspiring journey and would like to be featured in this series? Please send an email to or leave me a note in the comments below.