005: The #1 Mistake Killing Your Capital Raises (And How to Avoid It)
Raising Capital for Real Estate Investing
Release Date: 11/11/2025
017: Why Raising Capital Gets Harder After Your First Wins and What to Do Next with Tim Dowling
Raising Capital for Real Estate Investing
This coaching episode focuses on what it takes to raise capital beyond your first circle of investors. Amy Sylvis is joined by real estate investor Tim Dowling for an honest, real-time coaching conversation. With more than 20 years in real estate and experience spanning residential, multifamily, RV parks, mobile home parks, and large-scale development, Tim Dowling shares his real-world journey through multiple market cycles - and the challenge many capital raisers eventually face: evolving from organic, friends-and-family funding into a more intentional and scalable capital raising strategy....
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016: The Step You're Skipping That’s Costing You Investors
Raising Capital for Real Estate Investing
If you’ve been posting on LinkedIn (or thinking about it) and wondering why the leads aren’t turning into investors, this solo episode is your roadmap. Amy Sylvis breaks down the real reason your content might not be converting, and what to do instead. Using a heartfelt listener question as a launch point, Amy walks you through how to move out of "pipeline purgatory" and into consistent capital raising with content that speaks directly to your future investors. This episode unpacks the difference between talking about your journey and showing what’s in it for them. Because content...
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015: Why Your Investors are Ghosting You - And the 3 Steps to Fix It with John Todderud
Raising Capital for Real Estate Investing
In this powerful coaching episode, Amy Sylvis sits down with investor and capital raiser John Todderud to unpack one of the most misunderstood parts of capital raising: nurturing investor relationships over time. Together, they explore how to move beyond one-and-done outreach strategies and instead build real trust with potential investors - especially on LinkedIn. From what kinds of content actually work to when (and how) to follow up to whether AI can help, this episode is packed with tangible tips and candid wisdom. This episode is for you if you’ve ever wondered: Why do...
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014: How to Use Email to Turn Cold Leads into Eager Investors
Raising Capital for Real Estate Investing
If you’ve ever wondered why your emails aren’t converting or why your investor list isn’t engaging, this episode is your tactical guide to email marketing that actually raises capital. In this solo episode, Amy Sylvis shares the proven strategies her mastermind students use to create high-impact email campaigns - without sounding spammy or overwhelming their list. Amy walks you through the do’s and don’ts of investor emails that build trust, keep you compliant, and help you raise more money - faster and more easily. This episode is for you if you’ve ever wondered: ...
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013: The 3-Step “Diagnosis” to Find the Real Problem When Capital Raising Has Slowed Down with Calvin Lowe
Raising Capital for Real Estate Investing
On this coaching episode, we talk with Dr. Calvin Lowe of Peace Equity about what it really takes to raise capital as a real estate investor, especially when your audience is made up of busy professionals who are new to syndications.’ Amy Sylvis coaches Calvin through the real questions and challenges capital raisers face. How to clearly explain what you do. How to answer investor questions about risk with confidence. And how to position opportunities in a way that builds trust rather than pressure. The conversation also explores how to stay credible and continue nurturing investor...
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012: The Secret Successful Capital Raisers Know (That You Probably Don’t)
Raising Capital for Real Estate Investing
If you’ve ever found yourself silently thinking “I just need any investor to wire money right now,” this episode is your wake-up call – and your roadmap to long-term success. In this solo episode, Amy Sylvis reveals the often-overlooked secret that seasoned fund managers and capital raisers live by: knowing exactly who your ideal investor is – and intentionally attracting them (while gently repelling the rest). Amy walks you step-by-step through the strategy that helps make your capital raises smoother, faster, and far less stressful. This episode is for you if you’ve...
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011: From “Sounds Interesting” to “Where Do I Wire?” The Lead-to-Investor Process Explained with Jerry Miller
Raising Capital for Real Estate Investing
Feeling stuck in your capital raising journey? You’re not alone – and you don’t have to stay there. In this powerful coaching session, Amy Sylvis is joined by experienced capital raiser Jerry Miller, who opens up about his struggles with reaching a capital-raising plateau. If you've built some traction, raised funds from friends and family, but now feel like you're spinning your wheels trying to reach the next level – this episode is for you. Together, Amy and Jerry walk through the exact challenges capital raisers face when trying to scale beyond their inner circle. You’ll...
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010: My Exact LinkedIn DM Workflow for Turning Strangers Into Investors
Raising Capital for Real Estate Investing
If you're a real estate investor, syndicator, or fund manager who’s exhausted from chasing flaky investor leads, tired of relying on friends and family, or stuck wondering where your next wire will come from, this solo episode is your playbook. Host Amy Sylvis pulls back the curtain on the exact strategies she’s used to raise millions organically through LinkedIn. No cold DMs. No awkward sales pitches. Just smart, scalable systems that actually work. This episode is for you if you’ve ever wondered: How do I find new investors beyond my current network? Why do investors...
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009: LP Trust on Autopilot - How to Get Investors Reaching Out to YOU with Keith Heckman
Raising Capital for Real Estate Investing
If you're a real estate investor, fund manager, syndicator, or capital raiser who's tired of falling short on capital raises, relying on friends and family, or feeling stuck without predictable investor commitments, this episode is your roadmap to growth. In today’s coaching session, host Amy Sylvis sits down with investor Keith Heckman to break down the real challenges capital raisers face - and how to move past them with confidence. You’ll learn tactical steps you can implement immediately to attract new investors, nurture relationships at scale, and convert interest into actual...
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008: Stuck on Your Raise? Try This 10 Minute LinkedIn Strategy
Raising Capital for Real Estate Investing
If you are stuck in pipeline purgatory or at a bottleneck breakpoint, this episode is for you. Pipeline purgatory is where many capital raisers land after their first couple of deals: friends and family are tapped out, referrals have slowed, and there is no consistent way to meet new, qualified investors. The bottleneck breakpoint comes next when you can raise money, but you have plateaued and cannot break through to larger or multiple deals because your investor pipeline is not growing fast enough. In this solo episode, Amy Sylvis shares how she moved out of both stages by treating...
info_outlineIn this episode, Amy and Jerome explore the evolving capital-raising landscape for real estate investors amid market challenges and shifts post-COVID. They reveal why thoughtful preparation and authentic relationship building, not just finding deals, are critical to sustainable success. Jerome offers deep insights on leveraging LinkedIn as a powerful tool to build trust at scale, creating repeatable systems for predictable capital raising capacity, and navigating investor psychology. Listeners will gain a strategic perspective on positioning themselves to thrive long-term while making meaningful community impact.
[00:01 - 04:12] Current State of Capital Raising
Capital raising is facing a tough "winter" season, with many investors doubting their choices.
COVID-19 significantly changed commercial real estate dynamics.
Many investors lose money from buying deals they shouldn’t have.
Success requires planting seeds now and nurturing them for future harvest.
[04:13 - 18:43] Building Relationships and Trust
Preparation is key; investors must know, like, and trust you before investing.
Start with friends and family; move to strangers gradually through relationship building.
Multiple touches and consistent, value-driven engagement build investor confidence.
Education and structured programs reduce costly mistakes and close knowledge gaps.
[18:44 - 27:06] Closing Deals and Sustaining Success in Capital Raising
Lack of capital raising capacity causes deals to fail and investors to exit the business.
Experienced operators and systems are essential; deals won’t close on just a good property.
Reputation is critical. Missed close damage credibility and future opportunities.
Knowing and managing capital raising capacity leads to confidence and repeatable success.
[27:07 - 30:20] Education, Persistence, and Impact in Capital Raising
Continuous education is critical to avoid costly trial and error in capital raising.
Friends and family capital is limited; to scale, you must build trust with strangers.
Reputation impacts not only deals but also community and resident well-being.
Capital raising empowers sharing time, talent, and treasure for meaningful community impact
Ready to take your real estate capital raising to the next level? Subscribe to Raising Capital For Real Estate Investing with Amy Sylvis for actionable strategies, expert insights, and supportive community guidance.
To connect with Amy or learn more, email her directly at amy@capitalraisingsecrets.com. You can also visit the website or follow the community on LinkedIn.
GUEST BIO:
Jerome Myers, MBA, CEPA, is America’s leading exit authority and a pioneer in addressing the emotional and psychological side of business transitions. After building and exiting a $20M division of a Fortune 550 company, he founded Exit to Excellence and developed the Founder’s Exit Paradox and N.E.X.T. Framework—tools guiding leaders through purposeful succession.
A sought-after speaker and consultant, Jerome has shared his expertise with MIT, EO, Vistage, and the Exit Planning Institute. He’s authored Exit to Excellence and Your N.E.X.T., and hosts the Your N.E.X.T. podcast, helping founders move beyond transactions to create enduring legacies.
Reach out to Jerome on his website.
HOST BIO:
Amy Sylvis is the Founder and CEO of Sylvis Capital, a real estate investment firm connecting investors to hands-off income opportunities. After a 13-year career in biotech, Amy turned to real estate to build passive income and financial freedom - despite facing lifelong challenges with cystic fibrosis. Today, Sylvis Capital has 2,694 apartment units, 208,000 square feet of flex industrial space, and $407M worth of assets under management. Today, Amy teaches fund managers, syndicators and capital raisers how to increase their capital raising capacity through her on-demand course LinkedIn Capital Raising Secrets and her mastermind Capital Connection Pros.
Tweetable Quotes:
“Capital raising is one of those businesses where you have to put seed in the ground, you have to nurture that seed, and then eventually it grows and you'll be able to harvest it.” - Jerome Myers
“Find a good deal and the investors will come. I think a lot of us have heard that, and it's wrong. It is just wrong. What will work is creating repeatable systems and processes, because that's what capital raising is.” - Amy Sylvis
“The only way that you can continue to scale your business and get to, you know, several hundred millions of dollars like Amy has under management, is by getting strangers to know, like, and trust you so that they have the opportunity, when the time comes, to invest with you.” - Jerome Myers