Tough Love “REAL TALK” Advising/Mentoring for Entrepreneurs

— by “Realistic Rick” /


Yes, Optimistic is better than Pessimistic…
But REALISTIC is the game-changer!
Yes, Positivity is better than Negativity…
But OBJECTIVITY is the game-changer!

Our typical “Realistic Rick” Consult goes something like this:

  1. Let’s hear your elevator pitch.
  2. Ok… What is your top priority/goal? (Short-term? Long-Term?)
    X number of users? Y dollars in revenue? Z dollars in funding? in what T time period?
  3. How close do you think you are [to that milestone] — and what are the key steps to get there?
  4. One of these:
    a) Why/How/When do you think you’ll hit that next big target/goal?
    b) Why do you think an investor should give you money? — and/or — Why do you believe your startup will succeed?
[NOTE: In most cases, this is where “Realistic Rick” starts getting a little sassy and dispensing the “Tough Love” that most people are too (polite? afraid?) reluctant to provide] “Oh, you’ve identified a market need / gap / opportunity?? …and nobody else is doing this?? …or you’ll do it better and/or add something they’re missing? …all the feedback you’ve gotten has been positive/encouraging??
OH, you have the passion, hustle, and drive to do whatever it takes to succeed??

5. What percentages of startups/entrepreneurs do you think would have similar answers to the last few questions? (the same confidence, passion, belief, as you?)

6. What’s your “super-power” or competitive advantage? (Or, if cursing is acceptable “What are you really F*CKING GREAT AT?”)

7. I don’t want to see financials right now; but, from 10,000 feet… What do your projections show? [However YOU want to explain it…
X dollars in revenue (Year 1? 2?)
Y customers by (date?)?
Z% profit margin?
Customer Acquisition Cost?
Customer Lifetime Value?

*(Or you just kinda assume all the numbers will work out, you’ll have plenty of money to pay good salaries to enough employees, and yourself, and… Oh, you haven’t really thought that through yet?)

8. What are some of your key assumptions (that get you to one/some/all of your previous answers)… ?? — [I can explain/elaborate more on what I mean when we chat]


Let’s say we’re getting in a Time-Machine tonight and going (3? 5? 10?) years into the future to talk to “Future You”


“Future You” confirms your startup IS a SUCCESS!

We ask “Future You” to tell us what that means, what the company looks like, and what YOUR personal day-to-day life looks like. Can you imagine/guess/predict what “Future You” tells us??


“Future You” informs us that your startup FAILED!

Can you imagine/guess/predict what “Future You” will say when you ask “WHY/HOW did we fail?? What went wrong?!?”

(Which assumptions did you end up being wrong about? And when/how did you eventually recognize it and what did you do then?)
Persist & Pray? … Pause & Pivot? … Pivot & Persist? … Pull the Plug & Put an end to the Pain?]

Follow-Up Questions you will likely be asked several times after your initial responses above:

a) […] But WHY?
b) […] Do you KNOW that, THINK that, or HOPE that?
c) […] Is that based on a “Reliable OBJECTIVE Indicator” or an “Optimistic Assumption”?

SOME OF OUR MORE POPULAR #DiscussDebate Conversation Starters:

Negative and/or Pessimistic (is BAD?)
Positive and/or Optimistic (is GOOD?)
creates a dangerous false dichotomy!

Spoiler Alert: Objective + Realistic = GAME-CHANGER!

Multiple Perspective Thinking:
Helping you see your business from the perspectives of:
…customers / potential customers?
…employees / potential employees?
…investors / potential investors?
P.S. Ask us about other (controversial) perspectives we like to discuss :)

Lessons Learned from 500 FAILURES?!?
Listening to successful founders/advisors/mentors is great (keep doing it!), but you’ll likely never have the time/opportunity to learn from a statistically-relevant sample size of FAILED founders. Our ~10-year analysis of @500Failures helps us advise/mentor/coach armed with much more than just our own 1st-hand experiences.

#RealisticRick’s Tough Topics to #DiscussAndDebate
Unpopular Opinion: Most startups/founders (likely fueled by optimism/positivity/confidence) WAIT TOO LONG to ask “What IF we’re wrong about [X]?” (and/or to Proactively Ponder Potential Pivots?!). If ever there were a time to consider these questions objectively/calmly (with minimal emotional bias!), isn’t it now, BEFORE you’re actually FORCED to (while it’s still just a hypothetical?!)]

Helping YOU Challenge YOUR OWN Assumptions:
A — Assumptions: Do you KNOW it or THINK it or HOPE it?
B — Beliefs: Do you differentiate POSSIBLE
(“I believe I CAN do it!” = binary thinking)
vs. PROBABLE (full-spectrum)?
C — Confidence is great! …Depending what is it BASED ON?
[Data? Stats? Testing? (or Hunches/Feelings & the Conversion Rates YOU plugged in to hit YOUR revenue/growth goals?)]

***Contact for more info on working with us…. and/or, for a FREE “Realistic Rick” Consulting Session!

Spoiler Alert: *YOUR* “Startup” WILL Fail!
Now, let’s discuss WHY!
“Wait, what?? WTF?!?
What about Positivity?? Confidence?? Optimism??”

— SORRY, but “Realistic Rick” prefers Honesty, Objectivity, & Realistic Assumptions (based on Data, Probability, Statistics, and LOGIC!) Give it a shot… it’s a GAME-CHANGER!

P.S. Below are REAL testimonials from our “Realistic Rick” Consulting/Advising/Mentoring sessions:

  • Welp, that was a kick in the nuts
  • Every potential founder should be required to talk to you before they start!
  • … never would have thought that 15 minutes with [“Realistic Rick”] would be better feedback than my 150 customer discovery surveys [that I had done over] the past 30 days
  • This totally made me see how fake all my [friends/family] had been with encouragement [of my idea]… I went back to all of them, asked the right questions this time and [convinced them that] I wanted them to be totally honest, [and that I would take] no offense to whatever they said. Totally different feedback. Those fake-@ss motherf***ers made me waste a year of my life…
NOTE: This was BEFORE we created different session-length packages. They will definitely not all be 2-hours!
Full Disclosure: This was BEFORE the “Realistic Rick” persona was fully developed. So, “I loved the fact that I felt like I could have a relaxed conversation with you” will NOT necessarily apply to all consulting sessions. We would actually prefer to make you a little uncomfortable :)
  • … realized I had never actually thought about why I wanted to be an entrepreneur in the first place or why I had picked [this idea] to start… he definitely gave me a lot to think about! Would not recommend if you don’t take criticism [well] or [if you] get easily offended

***Contact for more info on working with us…. and/or to request a FREE “Realistic Rick” Consultation…



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