The Tryperion Holdings logo over an aerial photo of an apartment community with a pool, seen from under a white pergola.
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  • Reg D
  • Private Funds
  • 506(c)
  • 506(b)
  • Real Estate

Tryperion Holdings

From one REIT to the beginnings of a syndication marketplace

Alex Wills, Marketing Director at Streitwise and Tryperion Holdings, April 2018 to December 2024 (prior role), then a consultant.

  • $8.35M

    Investor commitments

    Two offerings, 2022 and 2023

  • $4.53M

    Victoria Multifamily Portfolio

    Rule 506(b), Victoria, Texas, 2022

  • $3.81M

    TH Trumbull

    Rule 506(c), Trumbull, Connecticut, 2023

  • $1.4M

    Attributed to Meta ads

    January to February 2023, within the TH Trumbull total

Alex's role: Marketing Director, leading marketing for both offerings. Commitments are the totals recorded for each offering. The $1.4M is the part of the TH Trumbull total that Streitwise's reporting attributed to Meta acquisition and retargeting.

Overview

Streitwise's investor business was built around a single Reg A+ Office REIT. As Marketing Director, I helped launch two multifamily syndications under Regulation D, the beginnings of a marketplace of real estate offerings. Together they recorded $8,345,460 in investor commitments in 2022 and 2023.

Tryperion Holdings is the private equity real estate firm behind Streitwise, and it managed the offerings. Streitwise is the brand investors knew, so this page uses Streitwise for the marketing and Tryperion Holdings for the firm behind it.

Bar chart of investor commitments: $4,530,533 for Victoria Multifamily Portfolio, a Rule 506(b) offering in 2022; $3,814,927 for TH Trumbull, a Rule 506(c) offering in 2023, of which $1.4M was attributed to Meta ads; $8,345,460 combined. Victoria Rule 506(b), 2022 $4,530,533 TH Trumbull Rule 506(c), 2023 $3,814,927 Combined Two offerings $8,345,460
Investor commitments recorded for each offering. The orange part of the TH Trumbull bar is the $1.4M that Streitwise's reporting attributed to Meta acquisition and retargeting, within that offering's total.

The opportunity

Give existing investors more than one offering

Streitwise had built its investor base around one product: a non-traded Office REIT, open to investors of all wealth levels under Reg A+. Office real estate was struggling after Covid-19, and the REIT was Streitwise's only offering. Separate multifamily syndications gave investors a different kind of real estate, and gave Streitwise a second way to raise capital.

Each new offering needed more than a campaign: a place in a broader marketplace, a different subscription platform, legal coordination, and an acquisition plan that fit its rule. The first offering could not be advertised publicly. The second could.

Goals and scope

Goals

  • Give Streitwise's investors real estate beyond the Office REIT
  • Launch each offering with an acquisition plan that fit its rule
  • Reach accredited investors beyond the existing audience
  • Keep the marketing within each offering's rules, working with legal

What I owned

  • Marketplace positioning
  • Offering launch
  • Juniper Square setup
  • Existing-investor outreach
  • Investor communications
  • Meta acquisition and retargeting
  • Google Search
  • Landing pages
  • Investor follow-up

Teams I coordinated

  • C-suite
  • Legal

The playbook

How the two offerings launched

  1. Moved a single-REIT brand toward a marketplace

    I worked with the C-suite to add the syndications and helped move Streitwise from one REIT toward a marketplace of real estate offerings. That meant connecting an established investor audience to new offerings, a different subscription platform, and acquisition suited to each offering's structure.

  2. Launched a 506(b) offering through existing investor relationships

    The first syndication was Victoria Multifamily Portfolio, multifamily real estate in Victoria, Texas, launched in 2022 under Rule 506(b). The rule does not allow general solicitation, so the offering was not advertised publicly. I focused acquisition on investor relationships Streitwise had built through its Reg A+ REIT, with legal coordination at the center of the launch.

    I set up the offering in Juniper Square, worked with legal to bring it to launch, and ran investor communications and fundraising marketing. Victoria Multifamily Portfolio recorded $4,530,533 in investor commitments.

  3. Launched a 506(c) offering with public marketing to accredited investors

    The second offering was TH Trumbull, for The Royce at Trumbull in Connecticut, under Rule 506(c). The rule allows general solicitation, provided every purchaser is accredited and the issuer takes reasonable steps to verify it. That opened a route to accredited investors beyond Streitwise's existing audience.

    I built the marketing for it: Meta acquisition and retargeting, Google Search, landing pages, qualification flows, and follow-up with investor education, webinars, and deal materials. The qualification questions sorted leads for follow-up. They were a marketing step, not the accredited-investor verification the rule requires.

    Streitwise's reporting attributed $1.4M of the offering's total to Meta acquisition and retargeting, which ran in January and February 2023. TH Trumbull recorded $3,814,927 in investor commitments.

    Facebook ad from Streitwise with Tryperion Holdings for a preferred equity opportunity for accredited investors only, over an aerial photo of an apartment community with a pool.
    A Meta ad for the 506(c) offering, under the Streitwise with Tryperion Holdings name. Terms in the ad described the offering when it ran and are not realized returns.
  4. Ran both offerings as one process

    I kept positioning, investor communications, campaign execution, and offering operations connected across both launches, so neither was a standalone advertising project. I also ran investor communications in Juniper Square, including funding updates.

Key moves

What changed

  1. A single-REIT brand moved toward a marketplace of real estate offerings
  2. A 506(b) launch built on existing investor relationships, with no public advertising
  3. Offering setup in Juniper Square, with legal involved from the start
  4. A 506(c) launch with public marketing to accredited investors on Meta and Google Search
  5. Qualification and follow-up through investor education, webinars, and deal materials
  6. Positioning, communications, campaigns, and operations run as one process

Results

The numbers

Commitments are the totals recorded for each offering in its entity dashboard. The $1.4M is the part of one offering that Streitwise's reporting attributed to Meta.

  • $8,345,460

    Combined investor commitments

    Two offerings, 2022 and 2023

  • $4,530,533

    Victoria Multifamily Portfolio

    Rule 506(b), Victoria, Texas, 2022

  • $3,814,927

    TH Trumbull

    Rule 506(c), Trumbull, Connecticut, 2023

  • $1.4M

    Attributed to Meta acquisition and retargeting

    January to February 2023, within the TH Trumbull total

Two entity tables from the offerings' investor platform: TH Trumbull with $3,814,927 committed and Victoria Multifamily Portfolio with $4,530,533 committed. Investor counts, called amounts, and parts of the entity names are hidden.
The offerings' entity dashboard, with investor counts, called amounts, and parts of the entity names hidden.

Results in detail

What the numbers mean

The $8,345,460 is the sum of two offerings' investor commitments: $4,530,533 for Victoria Multifamily Portfolio and $3,814,927 for TH Trumbull. Each is the committed total in the offering's entity dashboard.

These were separate offerings from Streitwise's Reg A+ Office REIT, so they are not part of the REIT's $20M+ total.

The $1.4M is investor capital that Streitwise's reporting attributed to Meta acquisition and retargeting for TH Trumbull in January and February 2023. It is part of that offering's $3,814,927, not additional to it.

Testimonials

From Streitwise's CEO and Forbes

Alex spearheaded the creation of several separate syndication offerings, helping raise $7.8 million.

His work includes strategic collaboration with the executive team on key decisions such as setting minimum investment thresholds and ensuring SEC compliance in the marketing campaigns.

His approach extends to the digital transformation of our investor portal, transitioning to a new platform with enhanced features that significantly improved the investor experience.

In addition, Alex's SEM strategies, content marketing, and paid campaigns resulted in a substantial increase in organic traffic, while his website redesigns and lead funnels formed the backbone of our marketing operations.

Jeffrey KarshJeffrey Karsh Co-Founder and CEO, Streitwise

First-mover advantage and aggressive Google advertising campaigns have allowed them to build the largest presence in the crypto-asset IRA space, with close to 4,000 customers and $105 million in inflows since they began accepting funds in June 2016.

Jeff Kauflin, Forbes The Hail Mary Retirement Plan: Bitcoin IRA, February 7, 2018

On Bitcoin IRA, where Alex led demand generation.

Key learnings

Learning Experiences

  1. The rule sets the marketing plan. A 506(b) offering and a 506(c) offering needed different acquisition from the first day.
  2. An existing investor base can support the next offering, within the rules. Legal belongs in the plan from the start.
  3. A new offering needs its operations ready before its marketing. The subscription platform, legal review, and investor communications came first.
  4. Public reach still needs follow-up. Ads started the conversation with accredited investors, and education, webinars, and deal materials carried it forward.

FAQ

Questions about this case study

How much of the $8.35M came from marketing?

Where a figure is attributed to one campaign, the page says so.

What is the difference between Rule 506(b) and Rule 506(c)?

Both are Regulation D exemptions for private offerings. Under Rule 506(b), the issuer cannot use general solicitation, such as public advertising, and can sell to accredited investors and up to 35 non-accredited investors who meet a sophistication standard. Under Rule 506(c), the issuer can advertise publicly, but every purchaser must be accredited, and the issuer must take reasonable steps to verify that status.

How does the marketing differ between a 506(b) and a 506(c) offering?

A 506(b) offering cannot be advertised, so it relies on relationships that exist before the offering, and counsel decides who can be approached and how. Being on a mailing list does not by itself create that kind of relationship. A 506(c) offering can use paid media, search, and landing pages to reach new accredited investors, so the work shifts to qualification, verification, and follow-up.

Can RaiseFM do this work on my Reg D raise?

RaiseFM works on the same parts of a raise: positioning, offering setup with your platform, investor communications, paid media where the rule allows it, and follow-up. Your counsel decides which rule applies and what the marketing can say. RaiseFM does not provide investor lists or introductions, and a past result is not a promise of funding.

Next step

The only fundraising consultant with direct platform and issuer experience. Work with Alex.

Share where the raise stands, the offering path, your timing, and the main challenge. Alex reviews every inquiry personally.

  1. You send a short inquiry: a few short questions about the raise, then how to reach you.
  2. We reply within one business day, whether or not the work is a fit.
  3. If it's a fit, you book a 30-minute first conversation from the link in that reply.

Tell us about your raise.

A few questions to help us understand your plans and where we can help.