Every week, my advisory calls end up circling around such radically different topics, I love the diversity of it all. 

Different founders with different companies in totally different stages. 

This is the messy, fun, complicated stuff. 

Here are 5 that came up this week and my no-bulls*t takes on each: 

1. Sales vs. Product: Should I keep polishing the product, or keep pushing sales?

Sales is the ultimate forcing function.

It puts pressure on product, ops, and leadership all at once. I would almost never suggest you take your foot off the gas unless you’re convinced that more customers in the short term would hurt you long term -- bad reputation, churn risk, or really poor delivery.

If none of those things are at play, then I’d focus on sales.

The truth is, most products are never “done.” 

But your customers will pull you toward the features that matter most.

2. Founder Compensation: How much profit should I actually take out of the business?

This is as much an emotional call as a financial one and obviously so different based on each person's unique situation. 

In my opinion, you should take as much as you need to live your life and stay clear-headed, but not so much that you starve the business of reinvestment.

If you’re constantly stressed about your personal finances, you won’t make good company decisions and you could burn out. Stability at home is obviously important. 

Just figure out that number that you can live with and make sure the rest is being reinvested in the biz to help you reach your goals. 

3. Comp & Benefits: As I start hiring full-time employees, which benefits matter most?

The moment you start bringing on full-timers, benefits begin to shift from “nice to have” to potentially being more of a trust signal. Employees hear all the time of startups going out of business, doing layoffs during tough times, etc. So naturally, they’re hard-wired to look for signs that your company might be different.

The clarity here for an early-stage startup is that you don’t need to match Fortune 500s, you don’t need insurance and 401ks and glorious 5-day Caribbean team retreats, but you should have a roadmap for the basics: health, PTO, some baseline retirement plan.

Even if you can’t roll them out on Day 1, showing a 12–18 month plan will communicate  seriousness and maturity and that will be important to most prospective employees. 

4. Go-to-Market: What should I do with a one-off group sale when most of my sales have been 1-to-1 or B2C?

Celebrate the win - you got a group to buy 13 high-ticket items! 

Then move on and do two things: 

  1. Study it. Why did they buy as a group? What pain point did it solve? How can you replicate it?

  2. Follow up fast to lock in future commitments, and use the data to test if you’ve uncovered a new channel or customer segment.

5. Product Validation: My customers are asking for “more” -- why not just build a high-priced product and launch quickly?

When existing customers want more from you, that’s a great signal, but don’t confuse signal with clarity. Instead of assuming you know exactly what “more” means, slow down slightly and validate with a beta or pilot. Ask yourself, “what’s the quickest way i can get a few data points to help me flesh this out more?” 

Talk to those customers, co-create, test a little bit before you set pricing. 

If you’re like me - and many founders - pricing is fun. Talking about sales is fun. Launching sh*t is fun.

But pricing a product that nobody ends up buying - or worse, that they buy & then churn - that’s a waste of time. 

Summing It Up

These are the quick, general frameworks I use to help founders cut through the noise.

Of course, every company is different -- industry, stage, team, and even more so, each owners personal goals all help to shape the “right” answer for them. 

But having a simple lens to start from keeps you from getting paralyzed, and keeps that momentum rolling! 

If you liked this blog post, you might enjoy this other one on i why i buy high & then buy even higher.

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