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Dalton + MichaelDalton + Michael

How To Get Better Advice

After doing office hours with thousands of Y Combinator companies over the years, Dalton and Michael discuss some tips and tricks on how to make the most of an advice session with an investor or mentor. Dalton + Michael is brought to you by @Standard_Cap Dalton Caldwell on X: https://x.com/daltonc Michael Seibel on X: https://x.com/mwseibel

Dalton CaldwellhostMichael Seibelhost
Nov 17, 202512mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

How founders can ask for advice that actually helps them

  1. Start advice conversations by explicitly stating what kind of help you want (decision-making, validation, tactics, or emotional support).
  2. Vague, open-ended prompts produce random or low-value guidance, so founders should come with an agenda and a clear definition of meeting success.
  3. Good advisors also set boundaries on what they can’t answer well (e.g., predicting customers, summarizing an entire industry, or doing broad investor lists).
  4. The most valuable advice often comes from identifying the “real problems” that cause anxiety (including morale and burnout), not superficial or filler topics.
  5. Founders should assess an advisor’s actual strengths using signals like operating background, technical interests, and portfolio patterns rather than surface-level bios.

IDEAS WORTH REMEMBERING

5 ideas

Ask upfront what kind of advice session this is.

Before diving in, clarify whether you want a pep talk, help making a decision, tactical debugging, or simply space to talk through hard feelings; it prevents misalignment and wasted time.

Don’t “shop for advice” to get permission for a decision you already made.

If you’ve decided to accept an acquisition offer (or reject it), recognize when you’re seeking validation and either own the decision or directly ask for the specific support you want.

Bring a tight agenda or you’ll get random advice.

Open-ended prompts like “tell me what to do” invite scattered feedback; specific questions (e.g., “Is now a good time to fundraise given X and Y?”) yield actionable guidance.

Surface the core issue early, not in the last two minutes.

Founders often avoid the real topic (runway, cofounders leaving, shutdown thoughts) and discuss minor items instead; naming the “aorta problem” unlocks the meeting’s real value.

Good advice givers draw a border around what they can’t answer.

Advisors can help prioritize and pressure-test thinking, but they often can’t reliably answer things like “what customers want” without context; explicit scope keeps advice high-quality.

WORDS WORTH SAVING

5 quotes

What kinda office hours is this? What advice do you wanna hear from me?

— Dalton Caldwell

If you already know what you wanna do… just like, do the thing.

— Michael Seibel

Tell the lawyer what you want and give them constraints. And then ask for legal advice.

— Dalton Caldwell

Hey, we’ve been shot eight places… Can we talk about the sprained ankle?

— Michael Seibel

The quality of what you give us is the only factor in the quality of what we give you back.

— Dalton Caldwell

Clarifying the type of advice desired“Shopping for advice” and validation-seekingMeta-advice vs tactical advice mismatchAgenda-setting and defining meeting successAdvisor expertise boundaries and scope controlLawyer analogy: constraints + desired outcomeSurfacing core issues vs “sprained ankle” distractionsHonesty and high-quality inputs produce high-quality outputs

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