Mac Miller, new year, new quota 😎

Hey there 👋 it’s 2025. New year, new quota 😎.

Much love to all you sellers with new, higher quotas in 2025. Be brave. You got this.

Last week, while working out in our garage, this song came on. Mac Miller was surely talking about his end-of-year quota:

Inside today’s edition:

• My 7 Wild Predictions for tech in 2025 that nobody asked for...

• Elite Sales Recruiter: “These are the questions you NEED to ask before taking that new role”

• What I’m working on to improve my sales craft in 2025

Let’s dive in 👉

My 7 Wild Predictions for tech in 2025 that nobody asked for...

Over the holidays, Caroline & I received a TON of holiday cards. Apparently that happens when all your friends start having babies.

But one holiday card really stood out. It came from my friend Chandan Lodha (co-founder of CoinTracker). Each year he includes audaciously bold predictions for the year ahead.

One of his bolder predictions last year was that the price of Bitcoin would surpass $100k during 2024. It was at $42k at the time. I thought he had lost his mind… but guess who was right in the end?

Hint: not me.

So, without further explanation, here are my own 7 wild predictions for tech in 2025 that nobody asked for:

1. Self-driving car fleets (i.e. Waymo) expand to the top 5 US cities

2. A company with an AI CEO makes the Inc 5000

3. Google abandons traditional search, and replaces it with a fully conversational AI assistant

4. Nvidia’s market cap drops by 50%, driven by real competition

5. Tesla starts producing aircraft

6. The number 1 selling video game is produced by AI and never ends

7. The AI valuation bubble “pops”, but legit companies continue to be built (like Ciro) 👀

So there you have it. If even one of those things comes true, you owe me a kombucha (I don’t make the rules).

What else am I missing? Are there other predictions that should be on this list? Have I lost my mind? Let me know…

Elite Sales Recruiter: “These are the questions you NEED to ask before taking that new role”

One of the biggest mistakes I see among under-performing sales reps is picking the wrong company to join in the first place.

You see it far too often … a top performer lands at a bad-fit company, underperforms (often through no fault of their own), watches their confidence plummet, and then struggles to land a better role.

So … how do you prevent this?

I recently got to ask Jake Citrano, one of the best sales recruiters on the planet. He also happens to be one of the nicest humans.

Jake has helped hundreds of sales reps find their next career step, and is the co-founder of ClosedWon Talent and Quota Hunters.

He shared with me a set of critical questions he recommends every rep ask before signing that offer letter:

1. Who was hired last year?

   • Get a sense of new-hire success stories (or lack thereof). If the company can’t point to promising new talent who’ve ramped well, that’s a red flag.

2. How did they ramp up?

   • Ask about onboarding. Is there a structured training program? Are there mentors for new sales reps? Solid ramp processes show how seriously a company invests in its people.

3. How are they doing now?

   • Find out if new hires are hitting or exceeding quota. Ongoing success (or lack thereof) can reveal a lot about leadership support and team culture.

4. How did the company perform in 2024 against performance goals?

   • Look for transparency. A company that’s hitting - or exceeding - its targets is typically a safer bet than one that’s regularly under-delivering with excuses.

5. What will my territory be?

   • Territory matters. A huge factor in your earning potential is how they slice up the pie—are you getting a fair and balanced piece or an afterthought?

6. And the more obvious ones (but still essential):

   • Average deal size: Know the typical ticket size to gauge how many deals you need each quarter.

   • Commission structure: Is it fair and transparent, or does it rely on complicated metrics?

   • Quota: Understand what’s truly attainable vs. what’s on paper.

In my experience, you can’t over-prepare when choosing a new sales role.

Digging deeper like this during the interview process helps you avoid “the wrong company” trap - one that could cost you time, money, and career momentum.

What I’m working on to improve my sales craft in 2025

Inspired by last month’s lessons learned, I’m hunkering down on my sales craft. Here’s are 3 things I’m personally working on right now:

• More deeply understanding my buyers. To me, this means asking second-level questions beyond the surface-level answers. Questions like “You mentioned this is a big priority - what’s driving that focus?”

• Being hyper-clear about my ICP. If it’s 2025 and you fit my ICP, I want you to know it. If I could tattoo my ICP on my head to make it more obvious, I would (Caroline said “no”, I can’t tattoo my head).

• Selling through stories, not features. The best sellers are master storytellers. They use story to paint a picture of the past, present, and future. And they use that story to help buyers overcome inertia and take action. This is a skill I’ve been wanting to double-down on developing for a while.