The Fine Print No One Reads - Until It’s Too Late | Dan Pascone with Chris Hilliard | Ep. 40

In this episode, Dan Pascone sits down with compliance veteran and Winnow Solutions co-founder Chris Hilliard to unpack the “fine print” most people never read until there’s a problem. They explore how agencies like the Consumer Financial Protection Bureau (CFPB), SEC, FDIC, and state regulators actually work, what protections you have as a consumer, and why terms and conditions, arbitration clauses, and loan disclosures matter far more than we’d like to admit.

You’ll learn how banks and fintechs keep up with 80,000+ rules across federal, state, and even city regulators, what “regulation by enforcement” is, and practical steps you can take as an investor or borrower: using fiduciary advisers, escalating complaints correctly, and even leveraging AI to summarize complex documents before you sign.

• The fine print is the real contract. Those terms and conditions you agree to in seconds define your rights, your lender’s obligations, and whether you can sue or are forced into arbitration. Ignoring them only helps the institution, not you.
• Many regulators share the job of protecting you. The CFPB, SEC, FDIC, Federal Reserve, OCC, state banking regulators, attorneys general, and even some cities all play a role in supervising products like loans, deposits, cards, and collections.
• State rules are a huge and growing part of the picture. As federal enforcement ebbs and flows, states often step in with their own licensing requirements, consumer protections, and even early AI rules, creating a complex patchwork companies must follow.
• Consumers have more protections than they realize, but they must use them. You can escalate complaints to a bank’s “office of the president,” state regulators, and federal agencies, and institutions usually must respond within specific timeframes.
• Technology and fiduciary advice can level the playing field. Using a fiduciary adviser and simple AI tools to summarize fine print can help you understand fees, interest rates, risks, and rights before you sign anything binding.

• [00:00] Dan tees up the episode: the “hidden rules” that determine how your money is protected or isn’t.
• [01:06] Chris shares his 20+ year career in compliance and why he cares so much about consumers, not just institutions.
• [02:47] The origin story of Winnow: 85+ licenses at a fintech and a realization that there had to be a better way.
• [05:15] What Winnow actually does for banks, credit unions, and startups and why even Y Combinator-backed companies use it.
• [11:23] Deep dive: CFPB, Fed, FDIC, OCC, SEC, FTC, and how their roles differ plus what’s changing under different administrations.
• [13:43] How AI and state-level rules are colliding, New York’s DFS, Colorado’s aggressive AI proposal, and industry groups pushing for balance.
• [18:28] Bringing it down to earth: how consumers are actually protected, and why timeframes and “plain English” disclosures matter.
• [21:44] Truth in savings, usury limits, reverse mortgages, balloon payments and why exotic products come with extra education requirements.
• [24:39] The problem with “regulation by enforcement” and why consumers must comparison shop and self-advocate.
• [26:36] Dan’s practical hack: paste fine print into an AI model and have it summarize the key terms and risks before you sign.
• [27:48] Lightning round: superhuman email, remarkable tablets, fountain pens, gratitude journals, and advice to a younger self.

Episode 40 of the Making Sense of Your Money podcast tackles a topic most people avoid: compliance and fine print. Host Dan Pascone welcomes guest Chris Hilliard, a career compliance professional and co-founder of Winnow Solutions, to explain how the “boring” parts of finance regulations, licensing, disclosures, and legal terms actually control a huge portion of your financial life.

Chris shares how his experience at large institutions and a fintech called Happy Money (formerly Payoff) led him to co-create Winnow, a regulatory research platform that tracks more than 80,000 requirements across federal, state, and even city agencies. He explains how complex it is for banks, credit unions, and startups to stay compliant when every state and sometimes cities like Chicago or Yonkers can have their own licenses and rules for lending, servicing, and collections.

The conversation then zooms out to cover the major regulatory bodies: the CFPB’s consumer protection mandate, the Fed and FDIC’s safety and soundness oversight, the SEC and FTC’s roles, and the growing influence of state regulators, especially on emerging topics like AI. Chris highlights how “regulation by enforcement” can create uncertainty, and how trade groups work to push for principles-based, practical rules.

Dan steers the discussion back to the everyday investor and saver: what protections do you actually have as a consumer? Chris walks through key concepts like usury caps, disclosure requirements (Truth in Savings, Truth in Lending), timelines for complaint responses, and special counseling rules for products such as reverse mortgages. He and Dan stress the importance of reading or at least understanding the fine print, escalating issues to the right place, and getting help from fiduciary advisers who are legally obligated to act in your best interest.

They also touch on a modern hack: using AI to summarize terms and conditions or prospectuses so you can quickly understand fees, interest, risks, and rights. The episode concludes with a lighter lightning round, where Chris shares his love of superhuman email, remarkable tablets, fountain pens, nightly gratitude with his family, and the advice he’d give a younger version of himself, eat better, spend fewer 17-hour days in the office, and be as generous and grateful as possible.

Dan: I’m Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast. Real conversations that help high earners make sharper decisions so their money works as hard as they do. This is episode number 40 and today I’m joined by Chris Hilliard of Winnow Solutions to break down the hidden rules that shape how your money is protected and sometimes how it isn’t. We dig into the Consumer Financial Protection Bureau, state regulators, and what every investor should know about the fine print and fairness. If you find this valuable, tap like and subscribe so you never miss an episode that helps your money make more sense.

Narrator: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders make smart, confident money decisions. Chris, thanks for joining the Making Sense of Your Money podcast today. Really excited to have you, man.

Chris: It is great to be here. I really appreciate it, Dan. Thanks for having me.

Dan: You bet. We have a lot we’re going to get into today, and I know our audience is going to want to hear your expertise on a bunch of issues. Compliance is such an important part of financial services as you know probably as well as anyone. I want you to give us a quick high-level overview of your background because I think it’s unique, and then share what you and your team help solve for today.

Chris: Sure. I’ve basically been in compliance my entire career. Not a lot of folks say, “Yeah, I spent a ton of time in compliance it’s awesome,” but that’s me. I started my career in compliance and have been there for over 20 years at this point now. I’ve worked at multiple large institutions like Lehman Brothers and AmeriQuest. I ran compliance for North America for State Bank of India. It’s been an interesting run.

Most recently, before Winnow, I was at a company called Payoff, now called Happy Money. We were an online financial wellness and credit card debt consolidation lender. We were the first fintech to partner with credit unions and really wanted to be member-focused. We didn’t think of people as customers we thought of them as members, extended family. That meant being upfront, using plain language, and having understandable notes and terms.

While I was there, we needed to get licensed across the nation 85 different licenses from one coast to the other, including credit services organization licenses, lender licenses, servicer licenses, debt buyer licenses, all of it. I had spent a significant amount of money with a great law firm called the Buckley firm to help us navigate that.

In talking with them, I kept saying, “There’s got to be a better way to do this.” There was a natural inflection point for me to leave, and I went to help found the company I’m at now, Winnow, with the Buckley law firm. Winnow is one of those businesses that wouldn’t be born out of private equity or VC. We spent three and a half years just collecting data all the privacy, compliance, and financial-services rules and regulations that govern financial organizations in this country at both the federal and state level.

There was a big lack of coverage on the state side when we got into the market, and there still really is outside of us. We spent a ton of time to ensure that folks know what they’re getting into, what they need to get into, and don’t have to spend the significant amount of money that we spent at a well-funded startup. With Winnow you can be a bootstrap startup and still get the information you need to figure out, Can I do consumer lending? Can I do commercial lending? Can I help folks get out of credit card debt? Do I need a license? Where do I need a license? That’s what really drove me first helping consumers get out of debt, and now helping consumers stay protected by making compliance easier for the companies serving them.

Dan: Okay, that makes a lot of sense. So at its simplest level, what does Winnow actually do, and what does it help institutions and ultimately consumers accomplish?

Chris: Winnow is an online state and federal regulatory compliance research engine. We’re a reg-tech company. If you’re already in business we have some great clients like Capital One and you’re a national bank, a state-chartered bank, or a lender with licenses, we bring that information into Winnow when you subscribe.

If you’ve got a charter or 25, 50, 100 licenses, we import all of that. Then when you go in and say, “I’m doing consumer lending; I need to know my late-charge disclosure requirements,” you can click a few times and get what we call a survey essentially what you’d go to a law firm for. You can see on a nationwide basis what you need to disclose and where. The second you save that survey, we’re monitoring it in the background. If anything changes, we let you know weekly with a redline from what was to what is, so you can quickly see what needs to be operationalized.

We cut out a lot of noise, so you spend less time trying to figure out what to even ask outside counsel. You just get directly to “here’s what’s changed, here’s what matters to us.”

We also allow up-and-coming startups we have a partnership with Y Combinator to access Winnow for free. They can figure out whether they really want to get into a particular line of business. For example, “Do I want to do consumer lending or mortgage lending in West Virginia?” The answer might be no, or “not yet,” because of that state’s regulatory scheme. Winnow helps you see what you’d need to do, what people you’d need to hire, and what it would cost to operate compliantly in the states you care about.

Dan: Got it. So you mentioned you had a previous relationship with Buckley, then that evolved into what you have today. Is Winnow staffed with attorneys? Contracted attorneys? Explain how that relationship works now and how those attorneys ultimately serve your clients.

Chris: The equity partners at Buckley were amazing. They literally funded Winnow out of their own compensation that’s how a law firm works if you’re going to invest in something. They were our biggest internal champions.

We’ve always been a wholly owned subsidiary of the Buckley firm, and we maintained that structure when Buckley merged with Orrick. We’re now a wholly owned subsidiary of Orrick, but we operate independently.

When we were doing the big data collection consumer lending, mortgage, credit card, auto, deposits, money transmission, earned wage access we needed access to a ton of attorney hours, and the firm gave us that. Once we finished that heavy lift, we didn’t need that many excess hours anymore. Now we have a team of four in-house attorneys dedicated to keeping Winnow updated tracking rule changes, new regulations, and making sure our content is current. They’re fantastic.

We built Winnow to be agnostic we spent a year and a half just building the data-entry tool. Technically, we could ingest insurance regulations, SEC, FDA anything but Buckley was a financial-services regulatory boutique, so that’s where we had the subject-matter expertise to start. That’s also where the market really lacked innovation and affordable tools.

Dan: Makes sense. Let’s shift gears and talk about the regulatory bodies. In my business, we’re regulated by the SEC previously FINRA, now as an RIA by the SEC but a big one in your space is the Consumer Financial Protection Bureau. That agency has gone through some transitions with different administrations. Walk us through the main governing bodies CFPB, Fed, FDIC, and the state regulators and how that’s evolved.

Chris: Great question. I’ll try to keep it relatively short.

The big one, as you said, is the Consumer Financial Protection Bureau, the CFPB. It was created after the financial crisis as an agency focused on consumer financial protection. Depending on the administration and who’s leading it, the CFPB has at times been very aggressive and at other times more hands-off, but it’s the main consumer regulator.

You also have the Federal Reserve Board, the FRB. If you’re a member bank, you’re subject to exams by the Fed. There’s also the FDIC the Federal Deposit Insurance Corporation that looks at safety and soundness and also compliance at state-chartered banks. If you’re a California state-chartered bank, for example, you might be examined by both the FDIC and the California regulator.

Then there are the broader agencies: the SEC, which you know well, and the FTC. They don’t just touch money directly, but they touch activities that involve money – securities, marketing practices, data privacy, things like that.

Under the current administration, we’re seeing a shift a pullback in some federal regulatory activity, and as that happens, states start to fill the vacuum. For example, there was talk of a 10-year moratorium on state-level AI regulations in an early draft of a big bill; that didn’t make it into the final version. States now feel free to act on AI. Previously, we had federal guidance from the White House on AI; now states like New York, through the Department of Financial Services, are being proactive with their own guidelines.

That can go sideways, too. Colorado, for example, nearly implemented a rule where if you did anything to train a large language model anything beyond using it off-the-shelf you were considered a “developer.” Developers were subject to ten times the rules of normal customers. That’s not sustainable. Fortunately, the legislature there delayed it and is revisiting the framework.

This is where trade organizations come in, like the American Fintech Council. They advocate for fintechs, lenders, banks, and credit unions. They push for rules that are appropriate not too reactionary, not too vague and for a principles-based approach instead of “regulation by enforcement,” where you only find out the rules after someone gets hit with an enforcement action.

On the state side, you have multiple regulators with their own licensing regimes. In California alone, you can lend under more than six different licenses: CRMLA, CFLL, small-balance lender licenses, and so on. Each license brings a different set of rules. You don’t want to over-license and subject yourself to requirements that don’t fit your business.

Multiply that patchwork by 51 plus Puerto Rico and Guam and you get the complexity we deal with at the state level. Most states aren’t talking to each other. There is an organization called the CSBS the Conference of State Bank Supervisors where they share information, but it’s not like the FFIEC at the federal level coordinating among agencies. CSBS is more of a forum than a command center.

Some states, like California, New York, Washington, and Illinois, tend to be more aggressive and set trends others follow. Other states, like Iowa, Nebraska, Utah, and Wyoming, are more business-friendly and often host industrial banks and innovative charters.

All of that creates a complex regulatory environment federal, state, and sometimes even local, like Yonkers or Chicago having their own debt collection licenses. That’s the world we operate in.

Dan: Hence why your services are valuable. I can see it very clearly now.

Let’s distill this down for the average consumer, investor, or saver. You’ve described this complex system of overlapping regulators and rules. For a normal person, what protection do they actually have? How are they being protected on the banking side, credit side, investing side?

Chris: Great question. I’ll start with something we all do but probably shouldn’t: we scroll right past the terms and conditions and click “accept.” Inside that fine print is where the governing terms of your relationship live.

Ideally, you’d read it all. Realistically, at least skim or get a summary because that’s where you’ll find things like mandatory arbitration clauses where you waive your ability to sue in court and agree to binding arbitration and details about fees, interest, and how disputes are resolved.

From a protection standpoint, consumers have quite a bit on paper. If you have an issue, you can complain to your bank or lender, but you can also complain to regulators. The challenge is knowing who to go to, is it a national bank? Then maybe the OCC. Is it state-chartered? Then the state banking regulator. You can file complaints with state attorneys general as well.

Every regulated institution must respond to complaints within certain timelines usually 30 days, sometimes 60. They have to provide a substantive response in plain language.

There are also substantive protections: usury laws that cap interest rates, rules on how often payments can be due, and requirements for clear disclosures. A lot of that flows from the CFPB, the Fed, and state laws. For example, if you open a savings account, you’ll receive a Truth in Savings disclosure that explains your APY, how interest is calculated, fees, and so on. Mortgage lending has Truth in Lending and TRID disclosures so you can compare offers.

For more complex products like reverse mortgages there are even counseling requirements. You can’t get a reverse mortgage without going through counseling to make sure you understand the implications, especially since these are often used by older homeowners and impact estate planning.

The information is out there you can go to the CFPB website and find consumer guides but it’s not always easy to navigate. That’s a weakness in the system. California, for example, does a better job than most states at publishing consumer-facing information, but even there you still need to do some digging.

Practically, for the average person, I’d say three things:

• Use your bank or lender’s escalation channels “Office of the President” or similar if you have a serious issue.
• Know that regulators exist and you can file complaints with them if you don’t get a satisfactory response.
• Slow down and compare offers, especially for mortgages, auto loans, and credit products. Don’t just take the first offer. Look at total cost, not just the payment.

And, as you mentioned later, using AI to summarize terms before you sign can be a great way to understand the fine print.

Dan: I love that. I’m a big believer in having an advisor or fiduciary advocate on your side whether that’s a financial planner like we have here or another professional to help you interpret the fine print and how it fits into your overall plan.

The other tip you touched on: don’t just sign off blindly. Take that disclosure, feed it into an AI model, and ask for a plain English summary of the key terms and what you’re agreeing to. Very few people will read everything line by line, but getting a summary before signing any financial document is a great best practice.

All right, great stuff, Chris. We’re going to shift gears and get to know you a little better. You are officially entering the lightning round. We don’t prep guests for this. It’s all about an organic first thought it can be a one-word answer or a longer explanation. Ready?

Chris: I’m as ready as I can be.

Dan: We’ll start with an easy one. Coffee or tea?

Chris: Tea. I don’t drink coffee. I like my caffeine carbonated, so it might actually be a soda in the morning which is terrible.

Dan: One meal for the rest of your life. What is it?

Chris: That’s a tough one. I’d like to live a decent amount of time, so I’d probably go with a really tasty salad like a chef salad, or maybe a salmon Caesar salad with not too much dressing.

Dan: That sounds good and something you could operate on for a while. Well played. What’s one tool or piece of technology hardware or software, but not your phone or computer that you can’t live without?

Chris: I use Superhuman for email.

Dan: Funny you say that I’m about to start using Superhuman. You can be my advocate then.

Chris: Superhuman is amazing. I can’t sing its praises enough.

Dan: Do you have a favorite quote or phrase about business or success?

Chris: I actually have a question written on my wall right now: “Who do you want to be right now?” I ask myself that multiple times a day. If I get into decision or task paralysis, I look up at that and ask, who do you want to be the guy stuck staring at the to-do list, or someone else?

Another one is from Richard Nixon, oddly enough. In his later years he said, “There are people who hate you, but they don’t win unless you hate them back, and then you destroy yourself.” I think in business that’s powerful. You don’t need to view competitors as enemies. Just focus on doing what you’re doing better.

Dan: That’s a really good one. I hadn’t heard that before. Do you have either a routine or a personal hack you can share with our audience?

Chris: I’m both analog and digital. I start every day with a handwritten to-do list. I spend the first few minutes getting everything out of my head. Then that list often morphs I’ll move it into my Remarkable tablet. Remarkable is a great product I love e-ink tablets because they don’t have the distractions of the internet.

I also keep physical journals and only write with fountain pens. I have terrible penmanship, so enjoying the pen helps. The key hack is to brain-dump everything so it’s not swirling around in your head. Then at the end of the day, my family and I sit around and do gratitude journals. It’s very simple we write down a few things we’re thankful for, like “I got a free slushie in the lunch line.” It doesn’t have to be profound. It just keeps us grounded and grateful.

Dan: I’m a big believer in end-of-day gratitude. I typically do it before bed, but you’ve inspired me to bring it to the dinner table. Last one: what advice would you give your younger self?

Chris: Eat better that’d be the first one. There were a lot of late nights with junk food, especially after Lehman’s bankruptcy. And second, you don’t need to spend 15–17 hours at the office to be productive.

Once I started working from home I’ve been doing that for about 15 years now I realized you can be incredibly productive without burning yourself out. Time with family matters. I’d tell my younger self you don’t have to be at work 17 hours a day. Nobody’s actually watching you for most of that time anyway. And I’d add: be as grateful and generous as possible. Help others whenever you can. Not everything you do has to benefit you. If it benefits someone else and improves their life, do it.

Dan: I love it. Really well said. That’s a great place to stop. Chris, thanks for joining us. If our listeners want to connect with you, collaborate, or learn more about you and your firm, what’s the best way to reach you?

Chris: Our website is winnow.law – that’s W-I-N-N-O-W dot law. I’m at chris@winnow.law if you want to email me directly. And on LinkedIn we’re Winnow Solutions. We’re very responsive – everyone on our team comes from a product, design, or compliance background, and we care a lot about user experience.

Dan: Very cool. Thanks for joining I really appreciate your insights. This was a lot of fun.

Chris: Thank you. This has been one of the best podcast experiences I’ve had. I appreciate how thoughtful you are with your guests, and I’d recommend anyone who’s on the fence about coming on your show to say yes.

Dan: Thanks a lot, Chris. That’s it for the episode. You can find our podcast along with our newsletter and YouTube channel, all for free, at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.

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