The Secret Weapon for Equity-Rich Executives | Dan Pascone with Adam Crawford | Ep. 33

In this episode, Dan Pascone talks with Adam Crawford, Head of Revenue at Cander, about one of the most underused tools available to equity-rich public company leaders: the 10b5-1 trading plan. They break down how a 10b5-1 plan works as a pre-set selling schedule for company stock, why it was created to protect insiders from accusations of trading on material non-public information (MNPI), and how it can now help a much broader range of employees automate diversification and taxes around RSUs, ESPP shares, and options.

You’ll hear how Cander uses technology to automate lot selection and tax-loss harvesting inside these plans, why relying on “log in and sell everything” or “never sell anything” behaviors can quietly increase risk, and how to align your trading plan with both company insider trading policies and your personal financial goals. If you’re a public-company leader sitting on meaningful equity, this episode shows how to turn a complex, stressful benefit into a systematic, compliant engine for long-term wealth.

• 10b5-1 plans are pre-set selling schedules for company stock. They’re legally binding contracts you adopt while not in possession of MNPI that then execute trades automatically later, providing an “affirmative defense” against insider trading claims.
• They’re no longer just for the C-suite. While 10b5-1 plans started as a tool for Section 16 officers and top executives, many companies now make them available more broadly sometimes to the entire employee base as an optional diversification tool.
• Your company’s insider trading policy is ground zero. SEC rules and your internal policy are separate. You can usually enter a 10b5-1 plan any time you could otherwise trade (open window and no MNPI), but you still need to read the policy and coordinate with your legal team before doing anything.
• RSUs, ESPP shares, and options can all be incorporated. Vesting RSUs, shares acquired through an ESPP, and option exercises can all be mapped into a single 10b5-1 plan, with each award type carrying its own tax implications that should be considered in the design.
• Automation can greatly improve tax outcomes. Cander’s platform automatically selects tax-efficient lots at the time of execution harvesting losses where possible and coordinating long-/short-term gains instead of forcing executives or advisors to pre-pick specific tax lots 12+ months in advance.
• 10b5-1 plans unlock trading during blackout periods. As long as the plan was adopted in a compliant way during an open window, trades can continue to execute even during blackout periods when you’d otherwise be prohibited from trading manually.
• Many employees fall into two unhelpful behaviors: “ATM” or “forever hold.” Some sell every share as soon as it vests; others never sell anything out of fear or inertia. A well-structured trading plan can create a more balanced, intentional path that aligns with an actual financial plan.
• Equity compensation should be a motivator, not a burden. Modern tools can reduce the need for employees to become market and tax experts just to use their stock grants. The goal is to translate equity into real-life outcomes tuition, homes, retirement without adding unnecessary stress.

• [00:26] – Dan introduces Episode 33 and frames the conversation around 10b5-1 plans as a “secret weapon” for public company leaders with significant equity.
• [01:14] – Adam shares his background: starting in stock plan services brokerage, earning FINRA licenses, running stock programs in-house through IPO and acquisition, and then joining Cander.
• [02:10] – What Cander does: helping public companies rethink equity comp, control market impact from employee selling, and give employees better tools to manage stock awards.
• [03:16] – Types of equity in scope: RSUs, ESPP shares, and (in some public companies) options all of which can be included under a single 10b5-1 plan.
• [04:46] – Dan lays out the twin goals: responsibly diversifying away from your employer while managing taxes carefully.
• [05:11] – Adam explains 10b5-1 plans in plain English: preset selling schedules and binding contracts designed to provide affirmative defense against insider trading accusations.
• [06:23] – Shift from executives-only to broader access: why some institutional clients now offer 10b5-1s to every employee as an optional diversification tool.
• [07:55] – For mid- and upper-level managers: how to think about eligibility, open trading windows, MNPI, and the need to coordinate with your company’s insider trading policy and legal team.
• [09:39] – Dan highlights why automation matters for busy professionals; Adam underscores the flexibility 10b5-1 plans provide to trade throughout the year, including blackout periods.
• [11:13] – Designing a plan for RSUs: Adam describes how Cander works with wealth managers and tax advisors to translate liquidity needs into rules within a plan rather than manual one-off trades.
• [13:36] – Taxes on RSUs: income at vest vs. capital gains afterward, plus the reality that many employees either sell everything immediately or hold forever.
• [15:06] – Tax-loss harvesting inside a 10b5-1 plan: automating lot selection across multiple RSU vests, ESPP purchases, and other lots to minimize tax where possible.
• [17:00] – Dan clarifies RSU tax misconceptions: you pay ordinary income at vest; holding is a choice about capital gains, not avoiding the initial tax hit.
• [19:40] – Monthly vesting, blackout windows, and special restricted lists: how 10b5-1 plans can help employees who are constantly in possession of MNPI (e.g., M&A, finance, research).
• [24:08] – Adam’s philosophy: equity comp should be a motivational, wealth-building tool not a source of stress that forces PhDs and senior leaders to become part-time tax experts.
• [25:42] – Dan’s perspective from advising clients: equity comp can be life-changing if managed well, but it requires structure and support.
• [25:55] – Lightning round: coffee over tea, steak and potatoes, Slack and Claude as favorite tools, Warren Buffett quotes, The Big Short, routines for remote work, and bucket-list experiences like the MuleSoft IPO.
• [30:22] – Where to find Adam and Cander: LinkedIn as the primary channel for learning more and connecting.

Episode 33 of the Making Sense of Your Money podcast features Adam Crawford, Head of Revenue at Cander, in a deep dive on 10b5-1 trading plans and why they’ve become a critical tool for equity-rich executives and public-company employees. Host Dan Pascone frames the discussion around a familiar tension: high earners accumulate meaningful company stock through RSUs, ESPP programs, and options, yet often struggle to diversify in a way that’s both compliant and tax-aware.

Adam begins by sharing his path into the stock plan world. He started as a finance undergrad, then joined a stock plan services broker right out of school and went through the FINRA licensing process. From there he jumped in-house at a client company, helping run their equity programs through an IPO and subsequent acquisition. That experience seeing both the broker side and the corporate side of stock plans eventually led him to Cander, where he now helps public companies rethink stock compensation, manage the market impact of employee selling, and give employees better tools to handle their awards.

At the core of the episode is a straightforward explanation of 10b5-1 plans. Adam describes them as formal, binding contracts that set out a pre-determined schedule for buying or selling company stock. The key is that they’re adopted when the employee is not in possession of material non-public information (MNPI) and during an open trading window under the company’s insider trading policy. Once in place, the plan “cools off” for a required period and then begins executing trades automatically, providing affirmative defense against insider trading claims because the trades are happening pursuant to a pre-set schedule rather than ad-hoc decisions.

Originally, 10b5-1 plans were almost exclusively used by top executives Section 16 officers and others who were always “in the know.” Adam notes that this has shifted. Some of Cander’s institutional clients now offer 10b5-1 plans to all employees with equity compensation, particularly those in functions like M&A, finance, or research who are routinely exposed to MNPI. Dan and Adam emphasize that the starting point for any employee considering a plan is the company’s insider trading policy and a conversation with internal legal; SEC law and internal policy are separate, and both must be respected.

The conversation then turns practical, especially around RSUs and ESPP shares. For RSUs, Adam reiterates that the tax treatment is relatively straightforward: when RSUs vest, their fair market value is taxed as ordinary income via payroll, just like a cash bonus. The real decision is what to do after vesting. Holding the stock exposes you to capital gains or losses, with a one-year holding period determining short- versus long-term tax rates. Dan points out a common misconception: many people think they need to hold RSUs for a year to “avoid” income tax, when in reality the income tax event already happened at vest.

Adam explains how 10b5-1 plans can incorporate multiple RSU vesting lots, ESPP purchases, and even option exercises into a single automated schedule. One of Cander’s biggest value-adds is automating lot selection and tax-loss harvesting at execution time. Instead of asking executives or their advisors to pre-select exact tax lots a year in advance, Cander’s technology factors in share prices, cost basis, and tax rules at the moment of trade to pick the most tax-efficient lots, aiming to minimize the overall tax burden while meeting liquidity and diversification goals.

Throughout the episode, both Dan and Adam return to the human side of equity comp. Many employees either treat their stock like an ATM logging in every quarter and selling everything as soon as it vests or they fall into the “forever hold” camp, paralyzed by complexity or convinced that selling shows a lack of faith in the company. Adam argues that neither extreme is ideal. Equity grants are meant to be motivational and wealth-building tools, not sources of stress that require every employee to become a tax and markets expert. With the right structure 10b5-1 plans, thoughtful financial planning, and modern automation equity can be systematically converted into the life outcomes people care about: homes, education, financial independence, and flexibility.

The episode wraps with a lightning round that gives a glimpse into Adam’s personality: coffee over tea, steak and potatoes as his forever meal, Slack as an indispensable tool (with Claude making a strong showing), admiration for Warren Buffett’s “fearful when others are greedy” mantra, and appreciation for stories like The Big Short that make financial history accessible. He also highlights the MuleSoft IPO as a career bucket-list moment and expresses his excitement about building Cander from an early-stage startup into a larger, lasting business.

Lightly edited for clarity and flow.

Dan: 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.

Dan: Welcome to episode 33 of the Making Sense of Your Money podcast. I’m your host, Dan Pascone, founder and CEO of Tailored Wealth. Each episode features a trusted voice in the financial world, bringing their expertise to help high achievers confidently make sense of their money.

Dan: Today I’m excited. We’ve got a great guest: Adam Crawford, Head of Revenue at Cander. He and his team specialize in 10b5-1 plans. So if you’re a public company leader, this is an episode you’ll definitely want to pay attention to. Adam, thanks for joining us.

Adam: Yeah, happy to be here, Dan. Thanks for having me.

Dan: We’ve got a lot to cover. Give the audience a quick overview of who you are, what you do, and how you ended up in this niche.

Adam: Sure. I started my career in finance I was a finance undergrad and went to work for a broker that specialized in stock plan services right out of school. I went through the FINRA path, became a licensed representative, and then eventually went in-house to one of our clients to help run their stock programs through an IPO and acquisition.

Adam: So I had a pretty comprehensive experience: brokerage side, serving employees, and then sitting inside a company going through capital markets transactions. From there, I had a couple more stops, including at Morgan, before joining Cander. I was excited to link up with Cander because they’re doing some really innovative things in the stock plan space, particularly around 10b5-1.

Adam: At a high level, we help public companies think differently about their stock compensation. We help them better manage the market impact of equity awards and provide their employees with much better tools to manage the retail float that’s being issued as equity comp. Before Cander, we felt that whole area was kind of a blind spot. Now we’re seeing it move the needle for companies and for employee-shareholders.

Dan: Love it. Let’s zoom out on equity comp first. A lot of our listeners have equity in some form, and we do a lot of content around this. What types of equity compensation do you and your firm work with most?

Adam: Our clients are primarily public companies, or very late-stage private companies that are about to list their shares. So we’re not usually dealing with early-stage private equity that’s totally illiquid. For public companies, we see a few main forms of equity comp.

Adam: The big one is restricted stock units RSUs. Another is shares acquired through an ESPP, an employee stock purchase plan. And then in some public companies, there are still stock options both non-qualified and sometimes ISOs. All of those award types can be contemplated in a single 10b5-1 plan.

Adam: As you know from your work, Dan, each award type has different tax implications. So understanding how they work, and in what order you sell them, can have a very material impact on someone’s take-home when it comes time to realize proceeds from those grants.

Dan: Totally. The two big challenges I see: first, how to diversify away from the company that’s also paying your salary; and second, how to do that in a tax-efficient manner. Those often clash.

Dan: Let’s dig into 10b5-1 plans. In plain English, what is a 10b5-1 plan and who is it for?

Adam: The simplest way to think about a 10b5-1 plan is as a preset selling schedule for your company stock. A level deeper: it’s a formal contract, a binding agreement you enter into in advance that sets out when and how you’ll trade your company shares in the future.

Adam: These contracts are designed to provide affirmative defense against insider trading. You adopt the plan when you’re not in possession of material non-public information MNPI and usually during an open trading window per your company’s insider trading policy. Then, after any required cooling-off period, the plan starts trading automatically. Because the trades follow a pre-defined schedule, they’re not based on you reacting to new information.

Adam: Historically, these plans were reserved mostly for executives Section 16 officers, C-suite leaders folks who are almost always in the know. It was hard for them to ever sell without raising questions. But that has changed. We work with clients today who offer 10b5-1 plans to every employee at the company as a diversification tool. Our mission is partly education: more people have access to these than realize it, and they can be very powerful when used thoughtfully.

Dan: I love that. There’s a big misperception that only top executives can use these.

Dan: Say I’m a mid- or senior-level manager at a public company and I have consistent RSU grants. The company doesn’t advertise 10b5-1 plans to everyone. Can I still set one up? What does that process look like?

Adam: I’ll caveat that I’m not a lawyer and don’t play one on TV. But broadly, if you’re being paid in company stock, you can likely access a 10b5-1 plan, as long as you follow your company’s insider trading policy and SEC rules.

Adam: The insider trading policy is ground zero. It’s a separate document from SEC law. It dictates when and how you can trade as an employee. So the first step is always to read that and talk with your internal legal team.

Adam: In general, if you’re in an open trading window and you’re not in possession of MNPI, you can trade your stock. That can include entering a 10b5-1 plan. From there, you’d typically work with a wealth manager, advisor, or a specialist provider like Cander. We handle the design and administration of the plan, but we don’t give individualized financial advice that’s where people like you, Dan, come in.

Adam: So: check the policy, confirm you’re clear of MNPI, get legal’s blessing, and then partner with a planner and a platform to set up the plan. But the key message is that mid-level or senior leaders often have more access to these tools than they think.

Dan: A couple things I really like about 10b5-1 plans. One is automation. For any busy professional, automating good behavior is huge. The second is that if you set up the plan during an open window, it can continue to execute during blackout periods, which solves a big pain point for many of my executive clients.

Dan: And then there’s the tax angle. So let’s use RSUs as our example since they’re common and relatively straightforward. When you’re structuring a 10b5-1 plan with someone who has ongoing RSU vesting, what are the main things to think about from a tax perspective?

Adam: With RSUs, taxes are conceptually simple. When the RSUs vest, they’re treated like a cash bonus the fair market value is taxed as ordinary income through payroll. The company withholds taxes, sometimes by selling a portion of the shares on your behalf. After that, what matters is how long you hold the shares and at what price you sell them. That’s where short- versus long-term capital gains comes in.

Adam: So step one is understanding cost basis the value at vest and the holding period for each lot. You can’t design a 10b5-1 plan intelligently without that. Step two is using the concept of tax-loss harvesting. Many executives have lots of different vesting lots at different prices. Especially with recent market volatility, some lots may be underwater. You can intentionally sell those at a loss to offset gains elsewhere.

Adam: Historically, building a 10b5-1 plan meant pre-selecting specific lots by hand, which is painful and imprecise. At Cander, we’ve automated that. Our system can dynamically choose the most tax-efficient lots at the time of execution, based on the share price, cost basis, and the tax rules, with an aim to get you as close to zero incremental tax as possible across transactions. That’s just not something a human should have to map out 12 months in advance in a spreadsheet.

Dan: That’s huge. If you’ve been at a company for years, you might have dozens of vesting events at different prices. Manually tracking which shares to sell when is a recipe for mistakes.

Dan: I also see a lot of confusion around holding periods for RSUs. People think they “have to” hold for a year. In reality, you’re paying ordinary income tax at vest either way. The year and a day holding period only affects whether later gains are taxed at short- or long-term capital gains rates. Can you speak to plans you’ve seen where people just sell immediately at vest?

Adam: Yeah, that’s a really important nuance. Before capital gains even come into play, RSUs are taxed as income at vest, through payroll. The company is effectively paying those taxes on your behalf from the vest value.

Adam: Once those shares hit your account, they’re yours. You can sell them immediately assuming you’re in an open window or you can hold them. Selling at or near the vest price means you’ve already taken care of the ordinary income tax, and any additional gain or loss will be based on future movements.

Adam: We tend to see two big behavioral camps. There are the “ATM” folks who log in every quarter and sell everything as soon as it vests. Then there are the “never sell” folks who just accumulate and hold indefinitely. There’s nothing inherently wrong with selling quickly it’s your money, and sometimes that’s the right diversification move but people shouldn’t feel like they have to hold for a year to make RSUs “work.” That’s a misunderstanding.

Adam: Again, the advantage of a 10b5-1 plan is that you don’t need to log in and make those decisions every quarter. You can design a rules-based schedule that gradually sells over time, balancing your tax, liquidity, and risk goals without constant manual intervention.

Dan: You mentioned monthly vesting schedules and the challenge of blackout windows. That’s something I see a lot too, especially with higher-level execs or people in sensitive functions. How do 10b5-1 plans help there?

Adam: For people with monthly vesting, some of those vests will always fall during blackout periods. If you’re not in a 10b5-1 plan, you might owe tax on vested shares and not be able to sell to raise cash. That’s not a great situation.

Adam: 10b5-1 plans, set up properly, allow trades to execute even during blackout periods. That’s especially valuable for people on what we sometimes call “restricted lists” or “special blackout lists” folks who always have MNPI because of their role. Think M&A, certain finance or strategy roles, research, etc. Even in an open window, they might be blocked from trading manually because they know things the market doesn’t.

Adam: For those employees, a 10b5-1 plan can be the only way to responsibly and legally monetize their equity. It’s one reason we’re seeing more institutional demand for expanding plan access beyond just the C-suite.

Dan: Let’s touch quickly on ESPP shares and how they fit into this. They’re a little more complex tax-wise, but once shares are purchased, how do they look in a 10b5-1 context?

Adam: ESPP programs let employees buy company stock at a discount, often via payroll deductions. Tax-wise, ESPP can be more nuanced more like incentive stock options in certain cases. But from a 10b5-1 standpoint, once the shares are purchased and in your account, they’re just shares. They can be treated like any other lot.

Adam: So within a 10b5-1 plan, ESPP shares become another tranche in the pool when the system is selecting lots to sell. The key is that whoever is running the plan understands the tax treatment of ESPP shares and incorporates that into the overall tax picture. The employee doesn’t need to manually tell the system which ESPP lots to sell; the technology should handle that within the rules of the plan.

Adam: For me, the bigger philosophical point is that employees shouldn’t have to become experts in all of this. When I was running stock plans at MuleSoft, I watched incredibly smart people PhDs, senior engineers struggle with the basics of equity comp, tax lots, and timing. That was a lightbulb moment. This is supposed to be a benefit, not a part-time job.

Adam: With the right tools and advisors, equity comp can be life-changing and still simple from the employee’s perspective. They should be able to say, “Here are my goals,” and have a system help translate their equity into those goals with minimal friction.

Dan: That’s a great point to land on. I’ve seen equity comp be truly life-changing for families but it’s also complex. It’s not as simple as a paycheck or even a cash bonus. That’s why I really like what you and Cander are doing to simplify and automate the mechanics so people can focus on what the money is actually for.

Dan: Let’s shift gears and get to know you a bit in our lightning round. First thing that comes to mind ready?

Adam: Let’s do it.

Dan: Coffee or tea?

Adam: Coffee.

Dan: One meal for the rest of your life?

Adam: Steak and potatoes.

Dan: One tool or piece of technology hardware or software other than your phone or computer that you can’t live without?

Adam: I’d say Slack, but Claude is making a run for it lately.

Dan: Favorite quote or phrase about money or success?

Adam: Probably Warren Buffett’s line: “Be fearful when others are greedy and greedy when others are fearful.” I first heard it in undergrad but appreciated it way more after seeing a few market cycles. Also, “Just buy the S&P” from the same guy is not bad advice either.

Dan: Favorite book on finance or business?

Adam: The first one that comes to mind is The Big Short. It’s educational and entertaining. On the heavier side, I’ve got Ray Dalio’s Changing World Order on my desk. It’s denser, very data-heavy, but great if you’re an economics nerd.

Dan: Any personal hacks you can share?

Adam: Nothing groundbreaking just routine. Especially working remotely, if I feel out of whack, it’s usually because I’ve broken one of my routines morning walks, workouts, that sort of thing. Whatever works for you, make it a habit.

Dan: Bucket-list item you’ve already accomplished?

Adam: Professionally, being part of the MuleSoft IPO. That was absolutely a bucket-list moment for me early in my career. Personally, I’ve been fortunate to travel to some amazing places that I would definitely count as bucket-list destinations.

Dan: One milestone you’re currently working toward?

Adam: At Cander, I’m really focused on building and growing the company. This is the earliest-stage venture I’ve joined around 15 people when I came on board. I’m excited to help grow it into an organization similar in scale to ones I’ve worked at in the past.

Dan: Last one: one piece of advice you’d give your younger self?

Adam: Listen to Warren Buffett.

Dan: You can always go back to Buffett. Adam, this has been fantastic. If our listeners want to connect with you or learn more about Cander, where should they go?

Adam: LinkedIn is best. Just search for “Adam Crawford Cander” and you’ll find me.

Dan: Perfect. Adam, thanks so much for sharing your time and insights. This was super valuable.

Adam: Thanks, Dan. Appreciate it.

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

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