Capital Conversations

In this episode of Capital Conversations, Karen Rands and Erik Nelson are joined by veteran securities attorney Michael Littman for a practical discussion about the legal realities behind Regulation A+ offerings and public company capital raises. With nearly five decades of securities law experience and more than 100 companies guided into the public markets, Michael brings a perspective few professionals can match.

The conversation explores what companies need to do before they ever file a Reg A+, why financial preparation is often the biggest obstacle to success, and how small mistakes in marketing, disclosures, or investor communications can create serious regulatory problems. They also discuss how public companies can use Reg A+ to raise additional capital, why general solicitation is such a powerful tool, and how companies can leverage crowdfunding without relying solely on venture capital or traditional investment banks.

One of the biggest themes throughout the episode is preparation. Strong financial records, experienced advisors, proper disclosures, and realistic expectations matter far more than most founders realize. Companies that approach capital raising strategically often create multiple future options. Companies that don't frequently discover their problems only after regulators, auditors, or investors begin asking questions.

Most founders focus on how to raise money. Far fewer focus on how to become investable. This episode explains why that distinction matters—and how companies can avoid many of the mistakes that derail capital raises before they ever get started.

In this episode of Capital Conversations, Karen Rands and Erik Nelson move beyond theory and into real-world examples of companies that used Regulation A+ and crowdfunding to raise capital, go public, and create liquidity for investors—with very different outcomes afterward.

They break down the explosive rise of Newsmax following its Reg A+ offering, why investor enthusiasm matters, and how audience loyalty can dramatically impact public market performance. They also examine companies like Boxable, ShiftPixy, Myomo, and Chicken Soup for the Soul Entertainment to show how crowdfunding can create opportunity even when the long-term business outcome becomes more complicated.

The conversation digs into something most people misunderstand about private investing: investors can still succeed even if the company later struggles. Timing, liquidity events, valuation, and market demand all matter—and those factors often determine outcomes more than headlines do.

They also explore how companies continue raising money after going public, how secondary markets create liquidity for early investors, and why understanding dilution, equity lines, and long-term capital strategy is critical for both founders and shareholders.

Most people only hear about crowdfunding when a company succeeds spectacularly—or collapses publicly.

What they miss is everything in the middle: the mechanics, the investor psychology, the capital strategy, and the way these deals actually evolve over time.

This episode gives a clearer look at how Reg A+ offerings behave in the real world—beyond the hype, beyond the fear, and beyond the headlines.

Episode SummaryIn this episode of Capital Conversations, Karen Rands and Erik Nelson analyze several real-world Regulation A+ and crowdfunding case studies, including Newsmax, Boxable, ShiftPixy, Myomo, and Chicken Soup for the Soul Entertainment.

They discuss how these companies raised capital, how investors achieved liquidity, what happened after the offerings, and the risks and opportunities associated with alternative public financing paths. The episode also explores secondary markets, equity credit lines, dilution pressure, valuation disagreements, and why strong investor appeal is critical in crowdfunding success.

You'll Learn:

• Why Newsmax became a breakout Reg A+ success story
• How investor demand impacts stock performance
• What equity credit lines and ATM offerings are
• Why dilution matters after an IPO
• How Boxable used crowdfunding and secondary markets
• Why valuation disagreements delay IPOs
• How secondary exchanges like Hive create liquidity
• Why ShiftPixy ultimately failed despite early success
• How Myomo used crowdfunding to support medical innovation
• Why investors can still profit even if companies later struggle
• What founders should understand before pursuing Reg A+ fundingEpisode Summary

In this episode of Capital Conversations, Karen Rands and Erik Nelson take a deep dive into Regulation A+ offerings and why they’ve become one of the most important capital raising tools for companies caught in the middle—too large for angel funding, too small for private equity, or simply outside the narrow lane venture capital firms typically pursue.

They break down how Reg A+ works, why it matters, and how it changed the landscape of private investing by opening equity opportunities to everyday investors instead of limiting participation to accredited millionaires and institutional money.

The conversation also gets into what most companies underestimate when they consider a Reg A+: the preparation, the marketing, the shareholder communication, and the strategy required to make an offering successful. Raising capital this way is not “build it and they will come.” Companies have to create visibility, investor trust, and momentum long before the raise closes.

They also explore how Reg A+ compares to Reg D, Reg CF, traditional IPOs, and reverse mergers—and why this pathway may become increasingly important as venture funding tightens and more companies look for alternative ways to scale.

Most founders assume their only options are banks, VCs, or giving up control to private equity.

That gap leaves a massive number of good companies stuck in place—not because the opportunity isn’t there, but because they don’t know another path exists.

This episode explains how Reg A+ works in the real world—so founders and investors can better understand the opportunity, the risks, and the long-term potential of this evolving capital market strategy.

In this episode of Capital Conversations, Karen Rands and Erik Nelson break down Regulation A+ offerings and how they give companies an alternative path to raising growth capital outside traditional venture capital and bank financing.

They explain the evolution of Reg A+, how it emerged from the JOBS Act, and why it represents what Karen calls the “democratization of the capital markets.” The discussion covers Tier 1 vs Tier 2 offerings, accredited vs unaccredited investors, testing the waters, marketing strategy, shareholder communications, and how Reg A+ can help companies bridge the gap between private and public markets.

The episode also explores real-world examples, including Newsmax and BrewDog, and explains why visibility, investor trust, and strategic communication are critical to a successful offering.

• What Regulation A+ offerings are
• The difference between Tier 1 and Tier 2 Reg A offerings
• How Reg A+ differs from Reg D and Reg CF
• Why Reg A+ is useful for “middle market” companies
• How general solicitation changed private investing
• Why marketing is critical to a successful Reg A+ raise
• What “testing the waters” means
• How Reg A+ can help companies prepare for uplisting
• Why shareholder communication matters
• How ordinary investors can participate in private offerings

Episode SummaryIn This Episode, You’ll Learn

Episode Summary

In this episode of Capital Conversations, Karen Rands and Erik Nelson take a deeper dive into IPO preparedness—what companies actually need in place before approaching investment bankers or entering the public markets.

They break down the legal, financial, and operational components required to be taken seriously in the IPO process, including corporate structure, proper stock issuance, audited financials, governance, and internal systems.

The conversation also explores how companies are evaluated by investment bankers, why preparation impacts valuation and access to capital, and how entrepreneurs can avoid costly mistakes that delay or prevent a successful public offering.

In the Episode You'll Learn

• What “IPO preparedness” really means and why it matters
• How to structure your company for public market readiness
• The difference between authorized vs issued shares
• Why improper stock issuance can block an IPO
• The role of securities attorneys (and why general attorneys aren’t enough)
• What PCAOB audits are and why they’re required
• How financial records and reporting impact capital access
• Why investment bankers pass on unprepared companies
• The importance of governance, boards, and internal controls
• How to position your company for valuation and investor confidence

Timestamps

00:22 — Welcome + episode recap and positioning
02:43 — Recap of prior episodes and show structure
05:04 — Erik’s background and capital markets overview
07:33 — IPOs vs acquisitions as exit strategies
10:40 — What is IPO preparedness?
11:58 — Why preparation matters to investment bankers
14:05 — How companies get in front of bankers (conferences, referrals)
15:03 — Corporate structure: C-Corp vs LLC
17:29 — Why public markets prefer corporations
20:31 — Authorized vs issued shares explained
21:54 — Why share structure impacts valuation
23:21 — Prior stock issuances and compliance risks
24:50 — Securities laws and exemptions (Reg D, 4(a)(2))
26:43 — Common mistakes in fundraising compliance
29:53 — Fixing past filing mistakes (Form D, etc.)
30:32 — Why securities attorneys are essential
31:31 — Not all securities attorneys are equal
32:51 — Industry conferences and networking (Planet MicroCap)
34:42 — Financial preparedness and audit requirements
36:09 — PCAOB audits vs standard audits
38:44 — Cost and timing impact of poor bookkeeping
41:13 — Business plans vs prospectuses
42:53 — Role of investment bankers in evaluating companies
43:39 — Market comps and valuation comparisons
45:35 — Unicorn valuations and market reality
48:12 — Venture capital dynamics and buybacks
50:03 — Forecasting vs forward-looking restrictions
51:15 — Financial models and investor scrutiny
51:41 — Corporate governance and board structure
52:56 — Exchange requirements (NASDAQ vs NYSE)
54:35 — Operational readiness and internal controls
56:39 — CEO role and investor relations
57:22 — Financial metrics and sustainability
58:47 — Crafting a strong investor narrative
59:10 — What makes a compelling company story
1:02:01 — Public speaking and leadership visibility
1:02:45 — Closing remarks and next episode preview

Episode Summary

In this episode of Capital Conversations, Karen Rands and Erik Nelson are joined by Richard Krieger, CEO of Moody Capital Solutions, for a deep, tactical conversation on capital raising strategies that most companies overlook.

Richard breaks down how rights offerings work, why they’re often misunderstood, and how they can be used to raise capital while strengthening—not harming—existing shareholder relationships. The discussion challenges common assumptions about dilution, discounts, and traditional financing methods like overnight deals and ATMs.

They also explore how market structure, investor behavior, and technology have evolved—and why companies that fail to plan ahead for capital needs often limit their own options.

In the Episode You'll Learn:

• Why rights offerings are one of the most underutilized capital raising strategies
• The biggest mistakes companies make when raising capital
• Why discounts don’t always mean more dilution
• How rights offerings align with long-term shareholder value
• The hidden risks of ATM (at-the-market) offerings
• Why short sellers avoid companies doing rights offerings
• The role of transfer agents in executing capital strategies
• How digital securities and blockchain are evolving the market
• Why timing your capital raise is critical to success

Timestamps:

00:24 — Welcome + introduction to Richard Krieger
01:50 — Podcast disclaimer
02:40 — Market recap: Dow Jones decline and support levels
05:04 — Chart analysis: why markets “fill gaps”
05:47 — Richard Krieger background and Moody Capital acquisition
08:06 — Lessons from the 2008 financial crisis
09:51 — Introduction to rights offerings
10:57 — Treating shareholders like customers
14:51 — How rights offerings reach all shareholders
18:28 — Why most companies don’t use rights offerings
20:30 — What companies get wrong about capital raises
21:48 — Key insight: discount vs dilution
23:21 — Case studies: Amco Pittsburgh, Cytosorbents, FlexShopper
24:44 — Who actually participates in rights offerings
25:23 — Risks and timing considerations
26:02 — Role of investment banks vs management
27:00 — Shift from roadshows to digital capital raising
28:22 — Investor behavior and transparency
29:02 — Problems with ATM offerings
31:14 — Why ATMs create uncertainty
33:19 — Short selling risks during rights offerings
35:39 — Short squeeze dynamics explained
36:21 — Overstock digital securities case study
39:37 — Blockchain securities and settlement challenges
42:47 — Evolution of digital trading infrastructure
45:32 — Rights offerings for OTC companies
46:25 — Reg A+ and raising up to $75M
48:47 — DTC and distribution advantages
50:08 — Why adoption of rights offerings may increase
50:26 — What’s next for Moody Capital
51:52 — Public vs private capital challenges
52:36 — Growth of corporate venture arms
53:07 — How to contact Moody Capital
54:04 — Final takeaway: shareholders are customers
55:16 — Choosing the right transfer agent
56:15 — Cross-border strategies and listings
57:24 — Mountain Share Transfer contact info
58:23 — Upcoming conferences
58:35 — Closing remarks

Episode Summary

In this episode of Capital Conversations, Karen Rands and Erik Nelson shift into their first “Hot Topics” discussion, breaking down recent market activity and what it means for investors and companies. They analyze the recent pullback in the Dow Jones Industrial Average, explore how market corrections impact IPO activity and valuations, and highlight opportunities that arise during volatility.

The conversation also dives into private market strategies, including crowdfunding success stories, venture capital dynamics, and why some companies are delaying IPOs. They wrap with a forward-looking discussion on regulatory changes, the evolving OTC markets, and the potential impact of the proposed Texas Stock Exchange.

• What the recent Dow Jones pullback means and how corrections are defined
• Why market downturns create opportunities for long-term investors
• The difference between public market volatility and private market investing
• How crowdfunding can lead to major liquidity events
• Why venture-backed companies are delaying IPOs and buying back shares
• What “unicorn” valuations really mean (and why they can be misleading)
• How OTC market changes and new regulations may impact capital formation
• What the Texas Stock Exchange could mean for competition and regulation

00:24 — Welcome + Hot Topics overview
01:00 — Disclaimer and purpose of the discussion
03:01 — Dow Jones overview and recent market pullback
05:02 — Market corrections vs bear markets explained
06:57 — Why downturns create buying opportunities
07:27 — Public vs private market investing differences
11:59 — Crowdfunding success story and liquidity outcomes
14:16 — IPO pricing, liquidity, and investor returns
17:12 — Share structure and capital strategy
20:40 — Why investors need to understand cap tables
23:14 — Venture capital behavior and liquidity strategies
24:40 — Why companies buy back shares before IPOs
27:21 — The truth about “unicorn” valuations
31:01 — Venture capital timelines and exit pressure
34:15 — OTC markets explained
37:26 — New OTC rules and “Expert Market”
40:20 — OTC ID and disclosure requirements
42:48 — Texas Stock Exchange discussion
46:46 — Regulation and SEC vs state dynamics
49:07 — FINRA’s role and market oversight
53:49 — Future of regulation and market competition
57:03 — Upcoming guest preview
57:53 — Where to follow Erik
58:55 — Closing remarks

In This Episode, You’ll LearnTimestamps

Episode Summary

In this episode of Capital Conversations, Karen Rands and Erik Nelson break down one of the most important milestones in business growth: going public. They walk through what an Initial Public Offering (IPO) actually is, why companies pursue it, and how today’s market differs from decades past.

The conversation expands into alternative paths to the public markets, including direct listings, reverse mergers, and SPAC transactions. They also explore secondary markets, liquidity options for early investors, and how capital raising strategies have evolved. The episode wraps with a discussion on cross-border listings and how companies choose between exchanges like NASDAQ and the NYSE.

What an IPO is and why companies go public

• How today’s IPO market differs from the past
• The role of investment banks in raising capital and pricing offerings
• What “lock-up periods” mean for insiders and investors
• How secondary markets provide liquidity before an IPO
• What direct listings are and when they make sense
• The pros and cons of reverse mergers
• How SPACs work—and why they can be risky
• What cross-border listings and ADRs are
• How companies choose between NASDAQ and NYSE

00:22 — Welcome + episode overview (IPO focus)
02:07 — Why IPOs matter for wealth creation and liquidity
02:52 — “It’s not 1985 anymore”: how IPO markets have changed
04:31 — Why companies go public today
05:50 — How IPO capital raising actually works
07:38 — Lock-up periods explained
08:23 — Secondary markets and pre-IPO liquidity
10:01 — IPO vs secondary offerings
11:48 — Reg A+ and private-to-public transitions
12:48 — Broker-dealers and alternative trading systems (ATS)
14:13 — Investment banks and IPO opportunities today
16:33 — What is a direct listing?
18:00 — Spotify example and when direct listings make sense
19:47 — What is a reverse merger?
20:58 — Why reverse mergers often struggle
23:46 — Common mistakes in reverse mergers
28:44 — What is a SPAC?
30:28 — SPAC risks and investor redemptions
32:49 — Real-world SPAC outcomes and pitfalls
36:40 — What are cross-border listings?
38:30 — ADRs vs ordinary shares explained
41:44 — NASDAQ vs NYSE: how companies choose
44:22 — Listing requirements and regulatory differences
46:33 — Exchange competition and perks
48:09 — Wrap-up + next episode preview

This is where it starts.

In this first episode of Capital Conversations, Karen Rands and Erik Nelson get into why they created the show—and what most people are getting wrong about raising capital. This isn’t a polished, textbook explanation of the markets. It’s a real conversation between two people who’ve spent decades inside it, talking through what actually happens behind the scenes.

They break down how capital markets really work, why so many companies get stuck trying to raise money, and the disconnect between entrepreneurs, investors, and the people advising them. If you’ve ever felt like there’s a whole system operating that no one fully explains, you’re right—and this is where it starts to make sense.

Most companies don’t fail to raise capital because the idea is bad. They fail because they don’t understand how the system works—how investors think, how deals are structured, and how capital actually moves.

That gap is expensive. It shows up as missed funding, bad terms, stalled growth, or going to the wrong people entirely.

This episode gives you the foundation most people skip—so you can make smarter decisions, ask better questions, and avoid wasting time (and money) chasing the wrong path.

SHOWNOTES:

https://sterlinginvestments.com/podcast-introduction-to-capital-conversations/

Welcome to "Capital Conversations," the LinkedIn LIVE podcast where we demystify the art of fundraising for privately held and publicly traded companies.

Join us each week as Karen Rands and Erik Nelson explore strategies for raising capital, preparing for initial public offerings (IPOs), and equipping investors with the tools to valuate growth potential. Erik & Karen's my professional alliance and friendship is decades long. They will be talking about the mistakes that business owners make in raising capital, going public, and staying public, wondering why it seems the same mistakes are made again and again. Part of it is because the rules are always changing, the other part is that they just don't know what they don't know. We decided to change that with are weekly podcast.

I hope you will join us. Each episode is scheduled for an hour to allow time for Q&A from our listening audience, but the main programming is targeted at half hour. Each episode will offer insights from our own real-world experiences, and then expand as we bring on guest speakers and panelists. Our goal is give you actionable take-aways and worthwhile 'aha' moments to put to work now, or add to your planning for raising capital or getting to an exit. Whether you're a business owner seeking capital, an established public company, or thinly traded company struggling to stay public, or an investor wondering how your investment in that private company can get to an exit - tune in for lively conversation between to friends that are 'old hats' in the space of finance, corporate compliance, and investing.