Episode 5 – The Power of Asking(and Why You Can Get Better at It)

Asking for what you want might be the most underrated skill in business.

This week on Founder Mode, Jason and I spoke with Andreas Homer. He’s a founder. He has built startups and made major deals at Microsoft. Now, he leads product partnerships at Shopify.

But what stood out most wasn’t his resume. It was how he built his career by asking. He made clear, bold, and honest requests that opened doors again and again.

One Ask Can Change Everything

Andreas told us how one simple ask helped him raise money, get great jobs, and hire the right people. The most important thing I took away was this:

Asking is a skill. And like any skill, you can get better at it with practice.

One of the first big asks I ever made was for a raise. I started at $40,000 in my first job. Soon, I moved up from junior engineer to team manager. I received a better offer from another company. So, I approached the CEO and said, “This only makes sense for me if I’m making $80,000.” And just like that—he said yes. My salary doubled in one ask. That moment taught me the power of being direct and knowing your value.

There have also been times where I asked for feedback and got more than I expected. It wasn’t always easy to hear. But even when the response was hard, I learned something. Asking means being open to the answer—even when it’s not what you want.

5 Simple Rules for Better Asks

Clarity matters
Skip the hints and be direct about what you need. Vague asks get vague results.
Be fair and respectful
Make sure your request makes sense for the other person. Give them space to say no.
Show conviction
If you don’t believe in your ask, why should they? Speak with confidence.
Master your timing
A “no” today might be a “yes” later. Stay positive and keep the door open.
Let asks lead to opportunity
Smart and intentional asks can quickly lead to job offers, funding, or important hires.

What I've Learned from Both Sides

Some of the best asks I’ve received were about mutual benefit. I've been invited to speak at events and join podcasts. These chances let us meet new people and gain visibility. One of the best was being invited to speak at UCLA—my alma mater. That talk took effort and time, but it created long-term value. Some of the students I met there later joined my companies.

When I was earlier in my career, I was scared to ask. These days, I’m more selective—not because I’m nervous, but because I want to be thoughtful. I don’t want to overstep or take advantage of a relationship. I’ve learned to ask with care.

I’ve also asked people to join companies, only to hear no. But that didn’t end the story. Years later, some of those people joined me, or I invested in their companies. A no today doesn’t mean no forever.