Walk in My Shoes.
On integration, regulated markets, and the role nobody hires for.
When DMX’s It’s Dark and Hell Is Hot blew up the hip-hop scene in the late ‘90s, nobody quite knew what to make of him or it. It was dark. It was brooding. He was integrating dog barking into his songs. Pitchfork put it best - “[the album was] a tragically clear-eyed criminal manifesto that dared to greet damnation with defiance and a psalm”. What has stuck with me over these years, even as my musical tastes have moved dramatically away from rap and hip-hop, is the grit in his lyrics. The guy lived a billion different lives - some grittier and more violent than others - and had a childhood and young adulthood that would make any sane person squirm. Yet he brought his whole experience into his music - and it landed. Five times. Five #1 Albums. You had kids like me in the suburbs of the San Francisco Bay Area blasting the fresh sound out of Yonkers, thinking nothing of the stories and horror he was processing through his lyrics.
Of all the lyrics I remember from my hip-hop phase, the stanza “walk in my shoes, hurt your feet — then you’ll understand why I do dirt in the street” has always stuck with me. It comes to mind when reviewing customer discovery. Writing a product roadmap. A board deck. Or, as evidenced here, when writing a blog post about startup strategy.
In Look Thru My Eyes, DMX gives the listener an invitation to step into his life and see it as he sees it. He pours his work, his struggle, emotions, parts of who he is, into an integrated life of experience compacted even further into a 4-minute song.
In startups, we do the opposite
CEO - building great companies that provide outsize returns for employees and investors
CMO - build enduring brands that foster enviable pipeline economics for a company
CPO - build products that delight the end user
CRO - own the number
VP of Safety - ensure products are built with best-in-class safety policies
VP of Communications - develop a narrative and create high-impact earned media opportunities
VP of Demand Generation - run paid media campaigns that lead to revenue generation
VP of Public Policy - make sure governments don’t make us testify or put us out of business
Etc.
But how often does the VP of Demand Generation think about the safety needs of the product and how the VP of Safety’s review of the product will make or break the ability for the Account Executive on the CRO’s team to be successful with their targets, who all care about security?
Or how does the CMO think about their multi-million dollar brand campaign and how their billboard and targeted ad blitz, complete with the VP of Communications landing a front page profile piece may rub a staffer, a lawmaker, hell - a Congressional Committee the wrong way and ultimately it’s their attempt to generate buzz that leads the VP of Public Policy to get a call that some lawmakers, and maybe an agency or two, want to meet with their CEO … if they’re lucky. If they’re unlucky, there's a hearing summons — and if they're really unlucky, a DOJ investigation. Maybe it’s just a misunderstanding, and while marketing consulted with Legal, they never thought to talk to Public Policy, or perhaps Safety, and now they’ve created buzz. Just not the kind they wanted.
This work lives in a specific window. At the seed stage, there's nothing to integrate — you're still chasing the ball. At the growth stage and beyond, the architecture is set, and the operators are entrenched in their craft with little appetite to question the structure they inherited. But at Series A through B, companies are still making foundational decisions that feel tactical but are actually architectural—whom to hire, how teams communicate, whether the regulatory landscape is a product input or an afterthought. Those decisions compound. In regulated markets, they compound fatally.
Steve Blank's customer discovery process, made famous in Four Steps to the Epiphany, and April Dunford's positioning framework in Obviously Awesome are the best work that exists on how to define who your product is actually for, and when actually used, are fire for defining where product-market fit exists and where your north star has to go.
Both methods begin with Customer Discovery. Interview your actual customers - makes sense, right? Everyone nods. Nobody wants to do it. The excuses are rampant: we don't want to waste valuable resources. We don't want to annoy our customers. Sales won't let us talk to them. Or my favorite — we don't have time for more discovery; we need to just build.
It's like running a political campaign without ever looking at a public opinion poll. Just vibes. Try selling that to a donor.
So founders insist they already know the customer. Product teams gatekeep advisory boards. Discovery, when it happens, is led-witness theater — "if we built this, would it help you do X?" — run internally with people who already use the product. The findings confirm what was already believed. The box gets checked. The conveyor belt moves.
I've watched this pattern destroy bets that should never have been made. Product teams who restricted customer access, ran their own validation, then reacted with fury when independent discovery — real conversations with real target customers outside the building — contradicted their assumptions. The project died. It should have. But it cost enormous political capital to kill, because by the time anyone did honest discovery, the organization was already emotionally and financially committed.
That's what step one actually looks like when someone does it right. Most organizations would rather skip it. Which is exactly why the rest of the steps collapse.
Government isn't a department. It's the medium. Most founders in regulated markets either ignore it or hire a government relations person and check the box. But a GR hire sitting on the G&A side — without product context, without GTM architecture, without commercial strategy input — is decoration. I know because I was that person. I came up through Congress, spent time in political campaigns and consulting — including work funded by Google and Yahoo — then went in-house at Microsoft before returning to the Hill. By the time I left government for startups, I'd seen how the largest corporate government affairs operations in tech worked — teams with eight- and nine-figure lobbying budgets, full legal and policy infrastructure, dedicated crisis communications. When I walked into my first startup, I assumed some version of that infrastructure existed. It didn't. I didn't even know what to ask for.
That experience led me into business operations for nearly a decade — because I realized that if I couldn't run a business, I had no business advising one on navigating government. Scaled companies like Microsoft, Google, and Amazon have GR teams in the hundreds, supported by business teams in the thousands. At startup,s they expect one person to do it all. That's not bad math. That's a suicide mission. And then when it goes wrong, the founder blames the hire.
To be clear, not every startup needs this integration. If you need a city agency to rezone your office building, hire a local GR person. If you're a biopharma with regulatory and compliance teams already embedded throughout the company, your GR person is there to get legislation through. Those are discrete functions with discrete scopes. But if you're building a sustainable business that operates inside a regulated market — driverless cars, Medicaid enrollment, healthcare delivery — the relationship between government and your product isn't a function. It's the architecture. And one person on the G&A side can't build that for you.
Everyone in startup land knows the "three amigos" — product, marketing, sales. The revenue side of the house. And when something's broken, the instinct is to add a fourth: a regulatory person, a GR hire, a compliance lead. But the problem isn't headcount. It's that legal, GR, and compliance sit on the G&A side — treated as overhead, not input. In regulated markets, the forces that will kill you are architecturally excluded from every decision that matters. You don't need a fourth amigo. You need a different restaurant.
The economics of healthcare delivery models don't work with what the government requires. This isn't a thesis — it's arithmetic. And every company that enters healthcare, assuming it can outrun those rules, ends up in the same place.
Forward Health charged $149 a month for tech-enabled primary care. Raised a $225M Series D and more than $650M total. Burned through it all. Shut down in November 2024. The customers cost more than they got paid. No amount of operational discipline can close a structural gap.
Papa — "Grandkids on Demand" — built an eldercare companionship model, funded like DoorDash. YC, SoftBank Vision Fund. B2C worked but wasn't large enough to meet investor return requirements, so they pivoted to Medicare Advantage payers. Here's where it breaks: the patients they were now serving — vulnerable elderly with complex needs — had demands that outstripped the skills and ability of their talent pool. To maintain VC-friendly unit economics, Papa kept caregivers classified as gig contractors. But you cannot serve a population with declining cognitive function, mobility issues, and real safety risks using a rotating cast of gig workers who cleared a background check. The talent model that made investors happy was structurally incompatible with the population it was asked to serve. This resulted in thousands of complaints, detailed reports of harassment and assault, a Senate inquiry, and CMS scrutiny. Papa still advertises partnerships with Medicare Advantage plans, but public reporting shows that a large swath of its MA and employer business was lost when nearly three dozen plans and employers chose not to renew.
And then there's Walmart — the largest company on earth. Walmart looked at Medicaid the way it looks at SNAP — a government payment mechanism it could optimize around through supplier negotiation. But you can't squeeze a nurse practitioner the way you squeeze a cereal manufacturer. Providers require a certain rate. You can't get lower-skilled workers due to regulations. And the Medicaid reimbursement rates on offer are not a priority for Walmart to lobby on, as they are not related to its core business. Regulation sets the floor on who delivers care, and Medicaid sets the ceiling on what it pays — and the gap between those two numbers is where Walmart Health went to die. Walmart ultimately announced plans to close all 51 Walmart Health centers in April 2024, despite talking about nearly doubling its clinic footprint earlier that same month.
The pattern is the same: the expectations are completely misaligned — in every direction. The government isn't going to increase Medicaid capitation. Medicare Advantage providers aren't going to pay more. Patients are desperate for care, but they can't afford it. Even people with private insurance and broader networks can't get quality primary care without paying a premium for concierge care. To provide that kind of care at Medicaid rates, you're either looking at taking humans out of the equation — which is where AI may eventually come in — or you're denying them care and letting hospitals deal with them showing up in the ER.
Forward and Papa died from integration failures that a strategic architect could have diagnosed. Walmart died from arithmetic nobody can change. The question for a founder isn't whether the rules apply to you. It's whether you're building for them or around them.
There's no title for this work because it sits between all the functions and above them all. That's why it doesn't get hired for — and why the companies that need it most don't know to ask.
Startups hire hammers. A CMO when they need demand. A government relations person, when regulators come knocking. A sales lead when the pipeline stalls. A product leader is needed when the demands of product management outstrip the CEO. Each hire solves the nail in front of them. Nobody's looking at whether the house is framed correctly. The role that does that — the person who sees where product decisions will trigger regulatory scrutiny, when your go-to-market motion will run headlong into payer constraints, which customer behaviors will create liability the gig economy playbook doesn't account for — doesn't have a clean job title. It sits between every function on the org chart and above the assumptions no one questions.
I built the instinct for this work before I had the vocabulary for it. At Cruise, I was hired as Head of Government Relations — but the company didn't have PR, a CMO, or marketing. The supporting infrastructure that every large organization I'd worked at took for granted simply didn't exist. So I built it. I created a framework from scratch for measuring the probability of legislative success in a potential market because nothing like it existed. I scaled our organization from zero to eight employees and more than a dozen consultants and vendors, with a $2.5 million budget, specifically to ensure that when a lawmaker was on the phone, there was someone to talk to, and when a colleague wanted to run a new product idea or GTM motion, there was someone to balance product and business with policy and political considerations. I wasn't filling a function. I was building the system that connected the functions — I just didn't know what to call it yet.
That experience sent me into a realization that changed the trajectory of my career. If I couldn't run a business, I had no business advising one on how to navigate government. So I deliberately moved — from a seed stage, pre-product startup where I was all things GTM plus product strategy, to a Series A head of marketing for data infrastructure, to a senior director of product marketing, to a senior director of product lifecycle management inside a corporate strategy team. Each move was chosen to fill a gap in my understanding of how companies actually work.
But the work that proved the model was customer discovery. As a senior director of product marketing, I was on a cross-functional business transformation team — the senior leaders of a billion-dollar business — trying to figure out how to integrate acquired products and bring them to market. My boss, the President of the company, gave me the budget and air cover to run a real discovery process. Jobs-to-be-done interviews, data analysis, mapping what customers actually wanted against what we had, what it would cost to build the gap, and what we'd realistically make. With a team of five and a ten-thousand-dollar budget, we completed fifty customer interviews in a month. The answer was that fit didn't exist — the market demand didn't match the product capability. That's not a failure of the acquisition thesis. That's what rigorous discovery is supposed to surface. We gave leadership the data to make a clear-eyed call before the company committed further, and they made it. The process worked — not because it was clever, but because it forced honest discovery in a system that had every incentive to skip it.
That work caught the eye of our Chief of Staff — soon to be Chief Strategy Officer. He saw the methodology wasn't a marketing exercise. It was a business architecture exercise that happened to be run by someone from the marketing side. He brought me with him when he stood up corporate strategy.
Corporate strategy is a role people roll their eyes at and say isn't real work. But if done well, it is the nerve center of a business — the General Contractor who came up through the construction ranks and built a rolodex to show it. I built the product lifecycle management process from scratch — a four-stage launch framework with heat map diagnostics, gap analysis, and a tiering structure that told leadership where to allocate resources. We launched fifteen products through that process. But what mattered wasn't the launches. It was that eighteen teams across a thousand-person company were finally working from the same map — with clear roles, clear stage gates, and a dashboard that showed where the gaps were before they became fires.
The people who learn these frameworks in corporate strategy or through Big Four consulting firms apply them to enterprise tech or the VC industry. Not regulated markets where the math doesn't work for startups trying to drive social behavior change. And the people who understand regulated markets never get inside a corporate strategy team — or hired into consulting beyond the government relations function — to learn the frameworks. That's the cross-section I sit in. I can define a company's current operating model, map where it needs to be based on where it wants to go, and bring all the teams together in an orchestrated way—not just to launch, but to build.
And your investors probably don't want you to hire for it. If your cap table expects you to scale like a SaaS company and isn't offering patient capital, this work looks like overhead. But companies like Forward, Papa, and Walmart didn't falter due to insufficient speed. They hit a brick wall building fast in the wrong direction — and in some cases, from inheriting the optimization function of whoever funded them. When your investors need a return on a timeline that doesn't match the physics of your market, every decision drifts toward what's fundable rather than what works. Not everyone can be Mark Cuban funding Cost Plus Drugs out of pocket — but more founders and investors should be studying why that model works when venture-backed healthcare companies keep dying. The question isn't whether you can afford to integrate these forces into your architecture. It's whether you can afford not to.
Nobody wants the whole person. People within industries tune out when you start talking about anything outside of what they see as their purview.
Capitol Hill, corporate government affairs, marketing, corporate strategy, product. Capitol Hill only wants to hear about Capitol Hill. Government relations only wants to hear about government relations. Marketing only wants to hear about marketing. Corporate strategy is focused on the company's growth prospects. You become a facade of a person — a caricature — when the language of these jobs bleeds into your everyday vocabulary and you start presenting yourself in whatever snippet matches the room you're in. And the system that fragments people that way is the same system that fragments companies — everybody hiring for the piece they recognize, nobody building for the integration they actually need.
Not because I couldn't pick a lane — because picking a lane is the problem. The founders who see human suffering and feel it's their responsibility to do something about it walk into a system where the conventional support structure was built for someone else entirely. The fundraising playbook, the hiring sequence, the growth metrics — all designed for SaaS. For markets where the physics reward speed. Not markets where the physics will kill you for cutting corners with a regulator.
The founders I respect are the ones who are okay with failure if they gave it everything. They're not okay with incompetence. They're not okay with treating people as unit economics or government as an afterthought. They understand that nobody gets to chase the hard technical quests — the higher-order visions — if the fundamentals are out of reach. Healthcare. Skills training. Dependent care. Housing access. These aren't market verticals. They're the infrastructure that determines whether someone gets to build a life in this country. That's what's at stake when we get this wrong. The work — the real quest, the hard one — is integrating these forces across the entire business so the mission stays alive long enough to matter.