Podcast Summary: "4 Mistakes First-Time Investors Make"

Podcast: Business School with Sharran Srivatsaa
Host: Sharran Srivatsaa
Date: November 11, 2025

Episode Overview

Sharran Srivatsaa delivers a tactical, straight-talking masterclass on the four most common mistakes that first-time (or early) investors make. Drawing from his own investing journey—from Wall Street banker to serial founder and prolific deal maker—Sharran breaks down not only what goes wrong, but exactly how to avoid the common pitfalls that derail new investors. Using real stories, scripts, and simple frameworks, this episode is a must-listen (or read) for anyone starting to put capital to work.

Key Discussion Points & Insights

1. The Impact of Early Investing Mistakes

• The experience from first few investments shapes your confidence and future behavior as an investor. If your early investments lose money or go sideways, rebuilding trust with yourself and the process becomes much harder.
  • Quote:
    “Most of the times the first few investments that we make shape not just what returns we get, but...it shapes my confidence.” [01:37]

2. Mistake #1: Being Embarrassed to Show Ignorance

- The Problem:

• Many first-time investors pretend to understand things—out of ego or the desire to look competent—leading to poor decisions and costly mistakes.
  • Quote:
    “When I started investing, I would just pretend like I understood more than I did and just to make myself be and look cool. Looking back, clearly this was dumb.” [03:14]
• Nodding along without asking simple questions results in committing to deals you don’t actually get.

- The Solution:

• Prepare a script that gives you permission to ask basic questions:
  • “Hey, I’m a really simple guy. Would it be okay if I asked you a thousand easy questions?” [04:32]
• Join investor groups for your first few deals so you can learn collectively and not feel isolated or embarrassed by not knowing everything.
  • Quote:
    “My favorite way to invest is investing in groups...Different people in the group have different expertise, so they can kind of jump in and explain things in a much better way.” [06:01]

3. Mistake #2: Succumbing to Peer Pressure

- The Problem:

• It’s hard to say “no” when friends or people you respect invite you into a deal, especially if there’s social status involved.
• Many worry that declining will make them look poor, uninformed, or timid.
  • Quote:
    “Social pressure can be significantly more intense… because of the type of car you drive or the house you live in… It’s way more intense.” [06:57]
• People often either ghost (ignore follow-ups), make up fake excuses, or feign interest with unnecessary questions.

- The Solution:

• Use a direct, respectful script to protect both the relationship and your own boundaries:
  • “Hey, Jimmy, I’m going to pass on this one. I’m already committed to another opportunity for this allocation. Thank you for including me. I would love to consider a future one with you.” [07:28]
• Don’t ghost, don’t make false excuses, and don’t fake engagement if you’re not interested.
  • Quote:
    “The truth is very freeing. So please don’t make up fake excuses.” [09:45]
• Always respond to deals clearly, even if you decline—this keeps you in the loop for future opportunities and helps you see more deal structures.
  • Quote:
    “The more deals that I see, the more structures I can see. And the more structures I can see, the better structuring I can do for others.” [09:12]

4. Mistake #3: Trusting the Operator of the Deal Blindly

- The Problem:

• First-time investors often assume that the strength of the idea or asset is what matters. In reality, it’s all about who is executing the deal.
  • Quote:
    “Good ideas are sexy…but the operator, the person who’s wielding the sword, makes or breaks the deal.” [11:33]
• When things go wrong—and they almost always do—it’s the operator’s grit, integrity, and tenacity that determines whether you lose money or not.

- The Solution:

• Always vet the operator, especially if the deal is significant and you haven’t worked together before.
• Offer a mutual background check:
  • “Hey, Jimmy, we want to make sure that we are good partners to each other. For that, we’d like to offer a mutual background check where you can run a background check on us and call our references, and we’ll do the same with you.” [13:01]
• Emphasize diligence over trust or gut feel.
  • Memorable Story:
    Sharran lost more money than most people make in their careers because he invested with someone he didn’t vet:
    “He was running two sets of books…when I did [a background check], he had a felony. And I was like, okay, so…I would have at least asked him about it, and it would have given me a red flag.” [13:40]

5. Mistake #4: Chasing Trends and FOMO (Fear Of Missing Out)

- The Problem:

• Hot deals and trends come in waves: crypto, real estate, Airbnbs, forex, penny stocks, etc. The details change but the emotional pull remains.
  • Quote:
    “There’s always a season for hot opportunities...The FOMO is totally real. And this is where most kind of early investors get swept up in this excitement.” [14:24], [14:49]

- The Solution:

• Tie every investment decision to the next milestone or goal in your financial journey, rather than doing it just because others are.
  • Quote:
    “The way to solve that is to tie every investment to the next milestone in your journey.” [15:00]
• Examples:
  • If your next goal is to build 12 months of cash reserves, ask, “Does this opportunity help me achieve that?” [15:44]
  • Don’t contribute to a retirement account or buy Bitcoin if it doesn’t contribute to your immediate goal (like generating your first passive income check).
    • Quote:
      “You putting $63,000 in your SEP IRA is a dumb idea…If the goal is to generate your next passive income check…” [16:42]
• Remember: time and capital are not unlimited! Each sizable bet matters, and not every investment makes sense for you.
  • Quote:
    “I honestly thought that just constantly investing in things would make me wealthy…You don’t get rich by investing. That’s a myth. You get wealthy by learning to become a good investor.” [19:43]
• Reference: Warren Buffett’s punch-card analogy—imagine you only have 10 lifetime investments, and treat each choice with that level of care.

Notable Quotes & Memorable Moments

• On Asking Questions:
  “Hey, I’m a really simple guy. Is it okay if I ask you a thousand easy questions?” [04:32]
• On Saying No:
  “Hey, Jimmy, I’m going to pass on this one. I’m already committed to another opportunity for this allocation. Thank you for including me. I would love to consider a future one with you.” [07:28]
• On Vetting Operators:
  “When things go wrong—and I will tell you things always go wrong—you want someone that you trust in the captain’s chair…” [11:33]
• On FOMO:
  “The way to solve that is to tie every investment to the next milestone in your journey.” [15:00]
• On the Reality of Building Wealth:
  “You get wealthy by learning to become a good investor. There’s a big difference.” [19:43]

Timestamps for Major Segments

• [01:06] – Overview of the episode’s goal for first-time investors
• [03:06] – Mistake #1: Embarrassed to Ask Questions/Show Ignorance
• [06:24] – Mistake #2: Succumbing to Peer Pressure (incl. scripts for saying no)
• [10:50] – Mistake #3: Trusting Operators Blindly (and how to vet them)
• [13:59] – Mistake #4: Chasing FOMO and Hot Trends
• [15:46] – The Goal-Oriented Approach to Investment Decisions
• [18:38] – The Myth of Investing Your Way to Wealth
• [20:01] – Recap of Four Mistakes and Final Thoughts

Summary Table: 4 Mistakes & Their Fixes

| Mistake | Solution / Fix | |----------------------------------------------|-------------------------------------------------| | 1. Embarrassed to show ignorance | Ask simple questions, invest with a group, script for transparency | | 2. Succumbing to peer pressure | Use a direct script to decline, respond to all offers, never ghost | | 3. Trusting operator blindly | Always vet operators, propose a mutual background check | | 4. Chasing trends and FOMO | Tie investments to specific goals, ignore hype |

Conclusion

Sharran leaves listeners with a powerful message: focus not on investing for its own sake, but on deliberately becoming a better investor by learning and avoiding common traps. The difference, he stresses, isn’t in doing more deals, but in doing fewer things wrong.

Apply these frameworks to start your journey with intention, clarity, and confidence—and skip a decade of painful mistakes.