Empowering Beginners with Investment Strategies and Support
Our guest UpNext on the podcast is Diana Perkins, founder and CEO of Trading with Diana, a trading education company that helps everyday professionals build wealth through the stock market, without Wall Street jargon or shame.
I first met Diana through her lunch and learn power hour with the UpNext team inside the Retail Playground.
I was instantly drawn to the way she makes trading feel accessible, even to women like me who are not number savvy and get overwhelmed by taking financial risks.
In this episode, we chat about:
- Learning to invest when numbers make your head swirl;
- Reframing investments and finance strategies to make them approachable and doable for entrepreneurs with tiny steps that don’t risk it all; and
- How a $10 bracelet from Nantucket nudged her back into creativity and reminded her of her younger, entrepreneurial self.
If you’ve ever felt intimidated by the stock market, or wondered how to start building wealth while you’re also building a business, this conversation will help you view your money differently.
Trading With Diana’s Journey
Her love of finance goes way back: as a kid in Akron, Ohio, she was opening savings accounts, charging her sister interest on $5 loans, and meticulously sorting her allowance into “checking” and “savings” envelopes. A virtual stock competition in college lit up something big, and after a 20-year corporate career in finance and consulting, she finally took the leap into trading stock options full time.
Diana has mentored and coached hundreds of aspiring traders—from total beginners who are scared to press “buy,” to experienced derivatives traders refining their craft.
Through private coaching, women’s workshops, comprehensive programs, and a weekly educational stock pick subscription, she blends technical knowledge with relatable advice to help people, especially women, feel confident in leading financially independent lives.
KEY TAKEAWAYS
- Start small and start now. You don’t need thousands to begin investing. Even $10–$100 a month into a brokerage account can be a powerful first step.
- Save first, spend what’s left. Treat saving (or investing) like a non-negotiable bill—automate it, then build your spending around what remains.
- Use tools that match your risk tolerance. High-yield savings accounts, broad market funds, and simple “set it and forget it” strategies can work even if you’re risk-averse.
- Practice in a simulator before risking real money. Demo accounts from major brokerages let you trade with “fake” funds so you can learn the mechanics and build confidence. Diana mentions Fidelity and ETrade.
- Entrepreneurship is a mirror. Going out on your own magnifies both your strengths and your insecurities—and invites you to decide how to face them.
- Capture your “bam” moments. Collecting success stories, testimonials, and tiny wins can help you stay grounded and keep going through the messy middle.
Resources & Mentions
- Books Mentioned
- Profit First by Mike Michalowicz
- The Alchemist by Paulo Coelho
- The Lord of the Rings by J.R.R. Tolkien
- (Referenced) Ursula K. Le Guin – The Eye of the Heron
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Get connected to entrepreneurs and resources to help your business thrive with the Retail Playground powered by UpNext . Use our code FOL15 for 15% off your monthly subscription.
Connect with Diana:
- Trading with Diana – Coaching, workshops & programs
- Website: tradingwithdiana.com
- Instagram: @tradingwithdiana
- Grab Diana’s Free Beginner’s Guide to Smart Investing.
- It’s a simple playbook to help you start making confident decisions in the markets.
- She also offers a complimentary 30-minute 1:1 Discovery Call to explore your financial goals and how her programs can help you build confidence and independence through trading.
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