The Investing for Beginners Podcast - Your Path to Financial Freedom

AAR30 - How When You Start Investing Matters

Dec 30, 2025

Discover how your investing mindset is shaped by the market environment in which you start. Andrew shares his journey from the financially cautious years post-Great Financial Crisis. Meanwhile, Evan reflects on his overconfident entry during a bull market. They discuss the psychological aspects of investing, including recency bias and herd mentality. Practical tips for new investors include focusing on education, consistency, and avoiding FOMO. Ultimately, it's about building strong, personalized investment habits.

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ANECDOTE

Starting After The Great Financial Crisis

Andrew Sather bought his first share (Microsoft) around Thanksgiving 2012 and dove into investing using the iPhone Stocks app.
He started investing coming out of the Great Financial Crisis when fear and bond allocations dominated the conversation.

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ANECDOTE

Easy Gains Turned To Learning

Evan Raidt started investing in late 2021 during a strong post-COVID market and initially thought investing was "easy."
A short downturn in 2022 shifted him toward learning and passive index investing.

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INSIGHT

Three Market Start Timelines

There are three market 'start' timelines: up, down, or flat, and each imprints a different mindset on new investors.
Your starting market biases risk appetite and what you prioritize when evaluating stocks.

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How Andrew first started investing

01:47 • 52sec

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Post‑GFC fear shaping investor behavior

02:39 • 4min

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Why Andrew stayed frugal but kept investing

06:45 • 2min

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Evan's late‑2021 'this is easy' mindset

08:54 • 3min

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The moment Evan's mindset flipped

12:01 • 6min

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Three market start scenarios

18:12 • 2min

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Down‑market pros and cons

20:04 • 2min

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Greedy vs fearful: herd mentality risks

22:27 • 2min

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Flat market behaviors and risks

24:28 • 5min

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Practical takeaways: education, consistency, automation

29:51 • 4min

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Comparing timelines and focusing on your growth

33:54 • 30sec

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What new investors face today

34:24 • 3min

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Final advice: be yourself and avoid FOMO

You can download Evan’s free monthly budgeting spreadsheet here: https://einvestingforbeginners.com/budget/

In this episode of At Any Rate, Evan Raidt is joined by Andrew Sather to talk about something most investors don’t realize is shaping their decisions: the market environment you “grew up” in. Andrew shares what it was like starting to invest in 2012 in the shadow of the Great Financial Crisis—when fear was high, bonds were still considered “prudent,” and energy stocks dominated the conversation.

Together, they break down the pros and cons of starting in an up market, down market, or flat market, how recency bias and herd mentality mess with your judgment, and why the best antidote is simple: more education, consistency, and automation.

Topics Covered:

How your “starting market” imprints your investing mindset (up, down, or flat)

Andrew’s 2012 investing experience vs. Evan’s late-2021 experience

Recency bias, herd mentality, and why fear/greed can flip your decisions

Practical ways to stay grounded: education, consistency, and automation

Avoiding “next big thing” FOMO (AI hype, NVIDIA chasing, Buffett comparisons)

Timestamps:

00:00 Why your investing “timeline” matters

01:03 Andrew’s first stock purchase

02:35 Post-GFC mindset

04:30 2012 market vibe

05:30 Why Andrew stayed frugal but kept investing

07:05 Evan’s late-2021 start

08:35 “This is easy” mindset—and the warning from a mentor

10:25 The moment it flipped

13:45 Three market “start” scenarios

16:05 Down-market cons

18:30 Greedy vs. fearful

24:50 Practical takeaways

29:15 Andrew’s advice for new investors today

33:00 Closing

Resources Mentioned:

Free monthly budgeting spreadsheet: https://einvestingforbeginners.com/budget/

Email the team: equity@einvestingforbeginners.com

Email Evan: evan@einvestingforbeginners.com

Have questions for Evan or Andrew about getting started (or staying consistent no matter what the market’s doing)? Comment below or email Evan—he’d love to hear from you.

Remember, financial freedom is built one smart move at a time. Keep it simple, keep it steady, and at any rate, we’ll see you next time.

Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.

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