Dalton + MichaelLessons learned advising startups #startups
advising startups by focusing on stage transitions, not local optimization.
In this episode of Dalton + Michael, Lessons learned advising startups #startups explores advising startups by focusing on stage transitions, not local optimization Startup life feels existential and stressful at every stage, even though the underlying challenges change by stage.
At a glance
WHAT IT’S REALLY ABOUT
Advising startups by focusing on stage transitions, not local optimization
- Startup life feels existential and stressful at every stage, even though the underlying challenges change by stage.
- The speaker would advise founders better by prioritizing “getting between stages” (reaching the next phase) over optimizing performance within the current phase.
- Many companies avoid the difficult question of whether they can become a truly big, successful business because it forces uncomfortable truths.
- Instead of confronting fundamentals, teams often default to easier, incremental metrics-focused problems like monthly growth targets or adding $1M in ARR.
- This avoidance can lead to tactical progress while sidestepping strategic viability and long-term company-building questions.
IDEAS WORTH REMEMBERING
5 ideasOptimize for stage transitions, not just current-stage efficiency.
Advising is often more impactful when it helps a startup unlock the next phase (e.g., proving product-market fit, scaling go-to-market) rather than polishing tactics that don’t change the company’s trajectory.
Recognize that “existential” pressure is normal at every stage.
The feeling doesn’t disappear as the company grows; what changes is the nature of the problems, so founders need stage-appropriate focus rather than expecting stability to arrive later.
Don’t let incremental targets replace fundamental strategy.
Hitting monthly growth goals or adding ARR can be useful, but these can become distractions if the core question—can this be a large, durable business?—is unanswered.
Hard questions are often avoided because they surface uncomfortable truths.
Teams may choose tractable, measurable tasks when the real issue might be market size, differentiation, distribution advantage, or willingness to make a difficult pivot.
A good advisor forces the “big company” conversation early and repeatedly.
Instead of only coaching execution, the advisor should help founders pressure-test whether the business has the ingredients for outsized success and what must change to get there.
WORDS WORTH SAVING
5 quotesLooking back, we've worked at companies at all these different stages, and at every stage in a startup, it's stressful, things feel existential, um, at every stage.
— Unknown
But fundamentally, the stages are different.
— Unknown
And I think that maybe if I were to go back in time and kinda give myself some advice on how to advise founders better, I think that I would be spending more time trying to help founders get between stages, get to the next stage, and less time trying to help founders optimize at the stage that they're in.
— Unknown
I've met a lot of companies where I feel as though engaging in the question of how you could actually be a big, successful company is, is too hard.
— Unknown
So instead, we'll kind of engage in easier questions like, how do you hit your monthly growth goal? Or how do you, like, add another million ARR, right? Like, we won't tackle the major stuff
— Unknown
QUESTIONS ANSWERED IN THIS EPISODE
5 questionsWhat are concrete examples of “between stages” work (e.g., from idea to PMF, PMF to scaling) that advisors should prioritize?
Startup life feels existential and stressful at every stage, even though the underlying challenges change by stage.
How do you diagnose when a team is over-optimizing within a stage versus preparing for a necessary stage shift?
The speaker would advise founders better by prioritizing “getting between stages” (reaching the next phase) over optimizing performance within the current phase.
What are the “uncomfortable truths” that most commonly block a startup from becoming a big company (market size, competition, distribution, founder-market fit, etc.)?
Many companies avoid the difficult question of whether they can become a truly big, successful business because it forces uncomfortable truths.
How can founders balance near-term metrics (like monthly growth or +$1M ARR) with the harder question of long-term viability without ignoring either?
Instead of confronting fundamentals, teams often default to easier, incremental metrics-focused problems like monthly growth targets or adding $1M in ARR.
If a startup is consistently hitting growth targets, what signals would still indicate it may not become a large, successful company?
This avoidance can lead to tactical progress while sidestepping strategic viability and long-term company-building questions.
Chapter Breakdown
Startup life feels existential at every stage
The speaker reflects on having worked across many startup stages and notes that stress and existential pressure show up throughout. Even though the intensity is constant, the nature of the challenges changes as the company evolves.
Advising focus: help founders transition between stages
They describe a shift they would make in hindsight: spending more time helping founders move from one stage to the next. The emphasis is on unlocking the next phase rather than polishing performance within the current phase.
Avoiding “optimize where you are” traps
The speaker contrasts two advisory modes: optimizing within the current stage versus breaking into the next stage. They argue that too much time can be wasted tuning metrics when the real need is a step-change in strategy, product, or market fit.
The hard question: can this become a big, enduring company?
They observe that some companies avoid seriously engaging with whether they can become large and successful because it’s difficult and uncomfortable. This can involve confronting truths the team would rather not address.
Defaulting to easier metric goals instead of core strategy
Instead of wrestling with fundamental company-building questions, teams often choose more tractable targets like monthly growth goals or incremental ARR milestones. The speaker frames these as easier conversations that can mask deeper issues.
EVERY SPOKEN WORD
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