Freelance to Freedom: Freelancing Strategies to Get More Clients and Build Financial Freedom
What The Deck: Courtney Allen on making $2m on Upwork
24 Oct 2023
Can you make over 7-figures on Upwork? Courtney Allen is proof that it’s possible. Kiri reached out to Courtney after reading about her in an interview and using Courtney as an example in her group cohorts that if you get very defined and specialized in what you do, you can beast the freelance marketplace.This interview digs into how Courtney was able to make money in those numbers on a freelance marketplace, how to hire and manage a remote team, in order to grow to $1m and how to handle clients that may be upset with your work.Courtney Allen is currently residing in Korea, a lover of K-Pop and has a fun and bubbly personality that comes through in the interview. She offers a unique perspective on taking a chance on oneself and addressing the world's less glamorous challenges. Her remarkable journey of starting a business at a young age, following a layoff and debt, has evolved into a thriving seven-figure company with headquarters in two countries and a global remote team. This accomplishment stands as a significant achievement, highlighting her resilience and entrepreneurial prowess. She is a PowerPoint specialist and the CEO of 16x9 Design.Notable moments: 02:21 – Courtney on her Upwork strategy08:56 – The evolution of her career and overcoming debt12:36 – Her $20 promise and commitment to giving back15:40 – Moving to Korea21:38 – The team of contractors and employees at 16x924:47 – Courtney reflects on her growth as a leader28:51 – Going from 6 to 7 figures36:01 – Lessons learned from losing a big contract42:02 – On overcoming imposter syndromeConnect with Courtney! 16x9 Design - https://www.16x9design.com/LinkedIn - https://www.linkedin.com/in/couallen/?originalSubdomain=caInstagram - https://www.instagram.com/courtingadventure/Upwork - https://www.upwork.com/Asana - https://asana.com/ClickUp - https://clickup.com/Mentioned on the show:Corporate2Contract Group Coaching - https://www.corporate2contract.com/group-coaching CNBC Article - https://www.cnbc.com/2023/06/13/millennial-brought-in-millions-making-powerpoints-her-career-advice-.html I'd love to help you grow your freelance business! CLICK HERE to set up a zoom call.Take control of your finances and figure out exactly what you need to earn with The Money Mapper. ~This podcast explores the journey to financial freedom through freelancing, remote work, and having an online business, tackling challenges like imposter syndrome and burnout, while promoting a growth mindset, confidence, and the ambition to build a remote career with better work life balance, time management, and productivity, all through intentional mindset shifts, personal development, and learning to work smarter, especially when working from home or navigating a career change.~
No persons identified in this episode.
This episode hasn't been transcribed yet
Help us prioritize this episode for transcription by upvoting it.
Popular episodes get transcribed faster
Other recent transcribed episodes
Transcribed and ready to explore now
Before the Crisis: How You and Your Relatives Can Prepare for Financial Caregiving
06 Dec 2025
Motley Fool Money
OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
06 Dec 2025
All-In with Chamath, Jason, Sacks & Friedberg
OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
06 Dec 2025
All-In with Chamath, Jason, Sacks & Friedberg
Anthropic Finds AI Answers with Interviewer
05 Dec 2025
The Daily AI Show
#2423 - John Cena
05 Dec 2025
The Joe Rogan Experience
Warehouse to wellness: Bob Mauch on modern pharmaceutical distribution
05 Dec 2025
McKinsey on Healthcare