Founder Mode: Getting Good at Asking
Hey there! Welcome back to Founder Mode! This week, Jason and I talk about a key skill for every founder: asking for what you need.
Why This Matters to Me
I've learned something important in my journey as a founder. Success isn't just about working hard. It's also about knowing when to ask for help.
As founders, we often need things—money, advice, or a new team member. Many of us think we should do everything ourselves. But I've found that asking for help can speed up your success faster than going it alone.
It's normal to worry if you're asking for too much. But I've learned that asking is one of your most powerful tools as a founder.
Learning from Andreas
This week, we talked with Andreas Homer. He has launched several companies. He worked at with me Microsoft (post Acompli). Now, he leads product partnerships at Shopify.
Andreas told me that asking has been key to his career. He's found that being real, clear, and honest helps one get exactly what one needs.
What I love about Andreas's approach is that he doesn't just focus on what he needs. He builds real relationships that help both sides. When you create value for others, they're more likely to help you. The more you ask, the more you learn, and the more doors open.
Learning from Andreas
1. Be Crystal Clear
Andreas said it's important to be clear about what you want. Many of us are too vague when asking for help. This makes it harder for people to know how to help us.
Think about it like this: Which question is better?
- "Can you help me with my business?"
- "I'm having trouble finding new customers. What worked for you?"
The second question is specific. It's clear what kind of help you need.
2. Focus on Win-Win Situations
The best business relationships help both sides. It's not just about what you can get; it's about what others gain from helping you. When you create value for others, you can form better connections.
I've seen this work in my own partnerships. That's the basis of a strong business relationship.
3. Don't Take "No" Personally
Every founder gets told "no" sometimes. This can come from VCs, clients, or new partners. Rejection is part of the journey.
But Andreas shared something important: "Every no is one step closer to a yes."
Rejection isn't personal; it's just part of the process. When someone says "no," don't see it as a failure. Instead, treat it as a chance to learn and grow.
When an investor turned me down, I felt discouraged at first. But I took the feedback, improved my pitch, and kept that door open. Six months later, they invested in my next project!
4. Ask for What You Really Need
Many founders ask for less than they actually need. We think asking for less will get us more “yes”. But Andreas suggests the opposite: ask for exactly what you need. This shows confidence, and you might just get exactly what you want.
5. Timing Is Everything
When you ask is just as important as what you ask for. Andreas shared how he used his network to connect with Shopify. It wasn't just the ask. It was about finding the right person at the right time and being real.
If you ask for something when a person is busy or stressed, you might not get what you need. But if you time it right—when they're open to your idea—it can lead to a win-win.
How to Start Asking Better
Start Small, Then Go Big
You don't have to make big asks right away. Ask for small things first, like advice, feedback, or help on a simple project. As you get more comfortable, you can move toward bigger requests. But always be specific about what you need.
When I started my first business, I began by asking for advice from a few trusted friends. I wasn't asking for money yet. Once I felt more confident and had a clear plan, I began asking for larger commitments.
Just Be You
Being real is key. Don't try to be someone else when asking for something. People can tell when you're not being genuine. Approach others with respect and clarity. If what you're asking for makes sense, people will usually want to help.
I remember my first big partnership ask. I wanted to seem like I had all the answers. Instead, I chose to be honest about what I knew and what I was still learning. That honesty helped us build trust.
Follow Up, But Don't Be Pushy
After you ask for something, it's okay to follow up—but be respectful about it. If someone says "no," keep the door open and stay in touch. The timing might change, and you might get the "yes" you've been hoping for.
I've found that a quick check-in email a few weeks later can keep the conversation going. Just don't push too hard or too often.
Know What You're Worth
Don't sell yourself short. When you ask for something, ask for what you truly need. Being confident in your ask often leads to better results. Believe in your value and let your ask reflect that.
I've had times when I hesitated to ask for what I deserved. I've learned to ask clearly and confidently. I'm often surprised by how well it turns out.
AI Tip of the Week: Exploring Cross-Chat Memory
A quick AI tip for the week: With more advanced LLMs now adding cross-context or cross-chat memory, you can ask them to review everything you've previously discussed. My friend Alex @ CreatorBuddy shared a fantastic post about prompting Grok (or other LLMs) to provide a summary of past conversations—an incredibly powerful way to leverage AI memory.
Check out Alex's post on Twitter here: Grok AI Prompt.
It’s a way to analyze past conversations to identify user strengths, blind spots, and propose market-aligned projects, a daily ritual, and a motivational mantra, citing memories in a concise, structured format under 600 words.
Kinda wild how well it works if you use AI a good bit.
Final Thoughts
As a founder, asking is a skill you must develop. The more you practice, the better you learn to connect with others and find opportunities. All entrepreneurs can learn from Andreas Homer's way of asking. He values clarity. He aims for mutual benefit and stays true to himself.
In our fast-changing world, we need help, support, and feedback. These things keep businesses moving forward. Those who know how to ask the right questions in the right way will continue to succeed.
Need a partner? Want to hire someone? Or just need advice? Remember, asking gives you power. Be clear, be real, and ask for what you need. You'll be amazed at the doors that open.
Your Turn!
If you liked today’s newsletter, please share it with someone who might need these asking tips. And I'd love to hear your thoughts! What's the best thing you ever got just because you asked for it?
See you next week,
-kevin
Recent Social Posts
Recent Podcasts
Catch up on past emails here.
2810 N Church St #87205, Wilmington, DE 19802
Unsubscribe · Preferences
