👨💻 Issue #62: Freelancing At Its Finest
Advice on straddling full-time vs freelancing careers and whether or not to make the entrepreneurial jump
💬 Welcome to issue #62 of Between the Lines
Good morning & happy Thursday. This past March, the U.S. saw a record 4.5M workers quit their jobs. Unsurprisingly, more are likely to follow; according to a recent PwC report, one in five workers globally plan on quitting in 2022.
This week, Jack Oliphant shares advice on determining whether the juice is worth the squeeze for those debating on shaking up their 9-5, and in particular, what a career in freelancing might look like.
~ Josh & Miles
📢 👥 Community Voices: Freelancing At Its Finest
Author: Jack Oliphant
Jack is a CMC ’13 graduate. He is a 2x-time Ironman finisher as well as a marathon enthusiast. For the last 8 years of his career, he has worked in digital media publishing and podcast advertising. In July 2021, he founded Oliphant Strategies LLC to provide sales and advertising solutions on a freelance basis.
With Insider article headlines like “Let’s admit it: Most managers are terrible” and survey findings like “83% of respondents believed they could do their job without a manager,” you may be asking yourself whether you still want that same 9–5 grind or if it’s time to shake things up. Whether it’s stagnation, frustration, or ambition, I want to help those who are teetering between full-time and freelancing by determining whether the juice is worth the squeeze and figuring out how to set yourself up for success by monetizing your skills and experiences.
In June 2021, I had just wrapped up a successful 2.5-year run; finally paid off my student loan debt; took a 3-month data analytics course outside of working hours, and found myself hitting a ceiling at my full-time job. Simultaneously, I had reached financial stability and was at a professional inflection point. Most of the time, I was incredibly happy with my employer, but three main pain points led to my frustration and my eventual resignation: pay, career growth, and healthcare.
Only you can decide your tipping point, if any, that would push you to leave an employment opportunity. However, regardless of your why, it’s important to prioritize your pain points and asks to your direct manager. And, if these asks are consistently not being met, it’s important to have tough conversations with your direct manager on timelines for when they will be met. Furthermore, if your requests are continually unmet in the timelines communicated, you may want to consider a jump.
Here are some ways to de-risk your jump while keeping in mind some lessons I’ve learned over the last year since I formed my own single-member LLC.👇
🚨Claremonster Call-Out: Maya Kale
After graduating from Claremont in 2016, Maya Kale headed for the startup world, joining foodtech company MealPal as their 15th employee in an operations role. She then spent the next four years at WeWork’s Singapore office in various marketing, operations, and leadership roles before founding Moom Health with her sister in 2021. Moom is a Singapore-based healthtech firm that creates natural remedies for modern women.
Moom offers supplements for women that can be used for hair treatment, skin treatment, stress removal, and sleep aid. Maya and her sister bootstrapped the company for over a year before announcing an $850K Seed round this week, led by the India/SE Asia consumer-focussed fund DSG Consumer Partners.
💼 Who’s Hiring?:
Co-founded in 2017 by Claremont alumnus Alexander Reichert, AgVend is the leading provider of digital engagement software to serve the producers of tomorrow. Their commerce portals are designed to strengthen the relationship between the ag distribution channel and their grower customers. Agvend operates a distributed organization model with local coverage in all major US and Canadian ag regions.
Their recent partnership with WinField United allows agriculture retailers to provide a premier, unified digital experience. They already count the most innovative cooperatives, independents, and national ag retailers as their partners, and they’re looking for more Claremont folks to join the team:
Yoodli is a startup building an AI platform to help people improve their communication skills without the pressure of an audience. They use AI-powered technology to provide their users with real-time and personalized feedback on their filler words, eye contact, pacing, and more. Founded by Pacific Northwest's Young Entrepreneur of the Year and Claremont alumnus Varun Puri, Yoodli is already being used by thousands of professional speakers, coaches, students, and corporate professionals to get data-driven insights on their speaking presentations.
They also recently raised $6M in a seed round co-led by Madrona Venture Group and Cercano Management. Check out their openings below to learn more about their team:
Check out the other ~5,000 open jobs at 400+ Claremont-affiliated companies here on our Storyboard. Plus, create a profile and enter your preferences to get alerted to new job postings relevant to you, be they the 1,000+ remote jobs, 100+ internships, or 40+ part-time positions available. We’ve published research that shows that Claremont-founded companies that disproportionately hire Claremont talent outperform — so pay attention, Claremonsters!
If any of these roles catch your eye 👀 , apply and mention Between the Lines. Or, if you are an employer looking to hire tip-top Claremont talent, fill out this form to have your jobs featured.
🗣️ Conversations on the Interwebz:
This week’s must-watch 📺
Autonomous vehicle company Cruise, co-founded by CEO and Claremont graduate Daniel Kan, was recently featured on the Today Show, showing off their new robo-taxi service in SF. Next stop, Cruise plans to head to Austin and Phoenix later this year.
Claremont financings 💸
WorkPatterns is a people management app that gives managers tools for unlocking the potential of their teams. The software development company was co-founded by Claremont graduates Noah Duncan and Dmitri Skjorshammer. They recently raised $4.2M, led by Javelin Venture Partners, Founders Fund, Zoom, and Merus Capital.
Tanoshi, co-founded by Claremont alumnus Brad Johnston, is an edtech company that helps close the digital divide by providing educational, affordable, and safe computers for school-age kids. They were recently selected to join Google’s Black Founder Fund.
This week’s top listen 🎧
Claremont graduate Josh Lewis is the CEO and co-founder of Sensible — the Twilio company for PDFs that transforms documents into structured data. He shares more about his career journey and the founding of Sensible.
Everything else you need to know💡
Congrats to Claremont alumnus and co-founder of Tixologi, Asher Weiss. Tixologi is a blockchain-based ticketing software that was recently included in Business Insider’s list of top retail startups in 2022.
Can’t get enough of Between the Lines? Follow and connect with us on Twitter!
🍽️ BTL Snacks:
⚕️ Next Era Of Pharma Leadership….. As the founder and chief scientific officer of Sparrow Pharmaceuticals, Claremont graduate David Katz is breathing new life into previously shelved drugs. PharmaVoice recently featured him as a trailblazer in the life sciences. Katz spent 18 years in Big Pharma as a leader in personalized medicine, drug discovery, and clinical trials at Abbott and AbbVie before founding Sparrow — a clinical-stage biopharmaceutical company backed by OrbiMed.
🌎 A Framework For Opportunity Sizing….. In theory, the Total Addressable Market is usually the easiest to size, but it can be incredibly deceiving in practice. The largest TAM markets oftentimes have the lowest ROI because they are some of the hardest to enter, grow, and make a profit. Claremont alumnus and angel investor Daniel Shi shares a more holistic framework for S-curve expansion that he learned during his six years at payments company Remitly.
🚲 The Metaverse For Sports….. Online exercise platform Zwift, founded by Claremont graduate Alarik Myrin, has launched its own turbo trainer, called Zwift Hub. Zwift is known as a destination of choice for cyclists using indoor trainers, with easy connectivity through whatever display device you have and a wide range of turbo trainers. They are now rolling out their own branded hardware.
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