Why “waiting for the right time” is costing you more than you think
A conversation about risk, timing, and why momentum favors those who move first
If you’ve spent any time around entrepreneurs or investors lately, you’ve probably heard some version of the same phrase: “I’m just waiting to see what happens.”
We’re on a pretty wild ride as a country at this moment, so waiting for rates to drop, prices to stabilize, or for “math to make sense again” might make perfect sense to you. Hell, It sounds rational. Cautious. Smart, even.
But here’s what’s actually happening while people wait: the investors who know how to operate — who understand how to structure deals, add value, and uncover opportunities others overlook — are out there building wealth. They’re not betting on timing. They’re making timing irrelevant by learning how to move in any market.
That’s the difference. Not some insider advantage or hidden playbook. Just a willingness to act while others hesitate.
Real estate, like entrepreneurship, rewards movement. It rewards those who are willing to get their hands a little dirty — and who can see opportunity in places that feel uncertain to everyone else.
Eggs! The Podcast guest and veteran real estate investor Alan Siebenaler didn’t start with perfect timing or deep pockets. He started with a bad financing deal, a fixer-upper condo, and a lot of questions. But he stayed in it. Over two decades and nine states later, he’s built a portfolio — and a perspective — that’s worth paying attention to.
Learning to Act While Everyone Else Waits — Meet Alan Siebenaler
Alan Siebenaler is a real estate investor and agent with over 22 years of experience, investing across nine different states and managing properties everywhere, from Culver City to Santa Barbara. His early story doesn’t start with money — it starts with constraint. He and his wife managed apartment buildings in exchange for rent, scraped together down payments when banks pulled the rug out, and learned the business not from a course but from surviving it.
But this isn’t just a story about real estate. It’s a story about acting when others hesitate. About finding leverage in the margins. About playing a long game before it looks like a sure thing.
Alan’s approach to investing mirrors the best kind of entrepreneurship — strategic, creative, and patient. He didn’t wait for perfect timing. He moved when things were messy, figured it out mid-flight, and kept compounding small moves into durable wins. His story isn’t about buying properties. It’s about building momentum.
What It Looks Like to Move When Others Aren’t Ready
“Five days before closing, the bank told us we didn’t qualify for zero-down after all. We were $3,000 short. I scraped together what I could. My grandma called and said, ‘Sweetie, I’ll loan you the rest — and you don’t have to pay me back.’”
The insight: Don’t walk away just because the plan changes. If the opportunity is good, get resourceful. Treat funding gaps as solvable problems — not deal-breakers. Make the call, ask the favor, and explore alternate paths.
“Sometimes our situations get really uncomfortable. That forces us to look at things we normally wouldn’t — and that gets us to the next level.”
The insight: When discomfort shows up in your business, don’t fold — just solve it. Use pressure to audit your assumptions and force better decisions. Ask: What is this problem trying to push me toward?
“I looked at that $70,000 check and thought, ‘I could go buy a Porsche.’ Instead, I bought a fourplex.”
The insight: When you come into unexpected cash — from a client, a sale, a windfall — pause before spending. Ask: How can I turn this money into an asset that makes more money? Default to investment over lifestyle.
“Flipping doesn’t build wealth. Holding does.”
The insight: Think in decades. When evaluating a new business line, investment, or opportunity, ask: Can this grow in value while I sleep? Prioritize moves that generate compounding returns — not just short-term income.
“You’re dating the interest rate — you’re marrying the property.”
The insight: Make decisions based on long-term fundamentals, not short-term conditions. Whether it's a new hire, partnership, or real estate deal — focus on the quality of the asset. You can always renegotiate the terms later.
“Creative financing is a skillset… I didn’t go through a bank. The seller financed the deal directly. No credit check, no appraisal — we made the deal work.”
The insight:
If the standard route doesn’t work, invent a new one. Ask: Who benefits if this deal goes through? Then, work backward from alignment. Structure terms creatively — not just conventionally.
“Real estate is just like shopping. The people who find the best deals are always looking.”
The insight:
Build opportunity-spotting into your weekly rhythm. Don’t wait until you need something to go looking for it. Keep scanning the landscape — clients, hires, investments — so you’re ready when it shows up.
The Advantage Belongs to the Ones Who Move
So the saying goes: The best time to plant a tree was 20 years ago. The second-best time is today.
Success — in business, in investing, in anything that compounds — rarely goes to the one who waits for certainty. It goes to the one who steps in early, learns by doing, and keeps moving while the rest of the room hesitates.
Alan’s story happens to be about real estate. But the lesson applies everywhere: don’t wait for perfect. Get in the game. Make the first move. Adjust as you go.
Because by the time everyone else is ready, you’ll already be holding the keys.
Thanks for reading,
—Ryan
Ready for more?
Catch Alan Siebenaler’s interview in its entirety on Eggs! The Podcast.
Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.
Path Picks
Cool stuff to help you forge your path to greatness.
Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R
Reading list
If you're looking to dive deeper into the ideas discussed in this piece, here are some recommended books and resources that align with Kyle McDowell's principles:
Rich Dad, Poor Dad by Robert Kiyosaki
The original spark for many first-time investors. Cliché or not, it still reframes the way people think about income, assets, and financial independence.The Psychology of Money by Morgan Housel
A modern classic on how wealth is built over time — and why your behavior matters more than your strategy. Especially powerful on timing, patience, and risk.Die With Zero by Bill Perkins
Not about real estate — about optimizing your life for action and experience while you still can. A gut-check for anyone stuck in “someday” mode.The Almanack of Naval Ravikant by Eric Jorgenson
A philosophical but practical lens on leverage, ownership, and wealth-building — without needing permission from gatekeepers.Buy Back Your Time by Dan Martell
For entrepreneurs looking to invest in systems and assets that pay you back — including your calendar. Strong tie-in to the theme of moving early and thinking long.
More to explore
Alan Siebenaler
https://www.linkedin.com/in/alansiebenaler/
https://ziagroup.com/team/alan-siebenaler/
https://www.instagram.com/alansiebs/
Work with me
Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio
R2 - Creative Services for Agencies and SMBs: https://www.r2mg.com
Eggs! The Podcast: https://www.eggscast.com
Would you like a personal introduction to any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.
Get featured
Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.