The first raise that failed and lessons learned

Real estate investor and former IT recruiter Janice Greenly joins Amy to unpack the real story behind learning to raise capital with confidence and intention. In this inspiring conversation, Janice shares how she shifted from corporate life to multifamily investing, the early mistakes that nearly derailed her first raise, and the systems that helped her transform failure into a repeatable process. From navigating friends-and-family raises to building credibility on LinkedIn and structuring investor education that earns trust, this episode sheds light on what it truly takes to grow from your existing network to a broader investor audience.

Whether you are new to capital raising or ready to scale, you will walk away with practical insights, mindset shifts, and a renewed belief that success is a learnable skill.

[00:00 – 04:40] From Recruiting to Real Estate: Janice's Path to Multifamily

• Left a long IT recruiting career after COVID created uncertainty

• Explored real estate as a practical plan B through education and mentors

• Closed her first multifamily deal with a strong team behind her Now passionate about helping others discover alternative wealth paths

[04:41 – 09:00] The First Capital Raise: What Went Wrong and What Was Learned

• Tried raising capital with no systems, no prep, and no education

• Early outreach felt rushed because people did not understand the opportunity

• Failure became a turning point for rebuilding the entire process Shifted to leading with awareness, education, and relationship-building

[09:01 – 14:30] Building Trust: Why Education Must Come Before the Ask

• Investors do not instantly view you as an expert just because you pivoted industries

• People need time to see your consistency and growing competence

• Syndicators often learn underwriting but not the business of raising capital

• Building trust requires patience, clarity, and regular communication

[14:31 – 24:30] LinkedIn Strategy That Works: Content, Consistency, and Connection

• Cold DMs rarely work because everyone is pitching on LinkedIn

• Content must speak to fears, goals, and real-life investor concerns

• Strategic commenting helps the right audience see your posts more often

• Send connection requests highlighting common ground, not investment asks

[24:31 – 32:00] Webinars, Education, and Becoming the Guide for Your Investors

• Monthly webinars help nurture leads already in your ecosystem

• Rotate topics like syndication basics, retirement funds, or asset protection

• Bring experts when needed to boost confidence and accuracy

• Repeating topics is useful because investors grow and forget over time

[32:01 – 38:00] Should You Pursue Large Check Writers? The Real Risks and Realities

• Extensive checks can fall through, creating major closing risks

• Large investors often seek control and influence over key decisions

• Retail investors can scale their commitments as trust builds

• Stability comes from many strong relationships, not a single source

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:

After a successful career as an IT recruiter, Janice Greenly shifted from helping companies find top talent to building businesses centered on long-term financial freedom. She began by launching a company in the essential services sector, providing energy, internet, and other everyday utility solutions. This entry into recession-resistant industries fueled her passion for recurring income and sustainable value.

Janice later expanded into real estate, where she now focuses on multifamily and self-storage investments in strong Texas markets. Her work centers on helping busy professionals grow their wealth passively, protect their time, and reduce taxes through smart, stable real estate strategies.

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: "Just because we decide to invest in real estate does not make us an expert in the eyes of our network. We have to earn that." — Janice Greenly "I failed miserably on my first raise, but that failure showed me exactly what I needed to fix." — Janice Greenly