Tough Love “REAL TALK” [advising? mentoring? dream-crushing?] for Entrepreneurs — by “Realistic Rick” (!)

It’s not what you WANT to hear — it’s what you NEED to hear!

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

  1. Let’s hear your elevator pitch.
  2. What’s your biggest priority/target/goal? (Short-term? Long-Term?)
    X number of users? Y dollars in revenue? Z dollars in funding?
  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) Tell us why you think you’ll hit that target/goal
    b) Tell us why you think an investor should give you money
    c) Tell us why you believe your startup will 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 thought that through yet?)

8. What are some of the key assumptions that get you there? (to one/some/all success indicator(s) from prior answers)… ? [I can explain/elaborate more on what I mean]

9. 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”
A) IF your startup is a success, can you tell me what that “success” actually looks like?
B) If, IF, *IF* your startup should fail, can you give your best guess (now) as to what “Future You” will say when you ask “WHY/HOW did we fail??” (Which assumptions did you end up being wrong about?) [When/how did you recognize that 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”?

***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. Real testimonials:

  • 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…
  • … 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, for a FREE “Realistic Rick” Consultation for YOUR Business, GO HERE:

P.S. If your business/idea is an area outside our comfort zone — [admittedly, we would be know help in areas like blockchain or A.I. or medical devices or FinTech] — I’ll probably have to decline so I’m not wasting your time (or mine). Be wary of ANYONE who says they can help you regardless of what your business is!

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