relentless iteration and dogged insistence

rules for a startup gap year.

My father has this rule: first, you have to exist. Then, you have to insist. Then, you have to persist. This startup gap year has been a masterclass in resilience.

Helm has been a lot of things over the past couple years. It’s a running joke: you guys pivoted again?

Our mode of operation has always been to fail fast and create actual value. We’re more naturally gifted as a product team than as a sales and marketing operation. If our product is valuable, then we have no problem marketing and selling it. But we’re not capable of propping up a poor product with elaborate salesmanship.

We’re also relatively new to the markets we’re building in. At a median age of 22.5, we haven’t had decades of industry experience, and we’ve had to work for every one of the thousands of insights we’ve collected. The upside? We don’t have decades of ingrained bias, and we offer a perspective that’s genuinely new to our industry.

up in flames

Recently, many highly regarded (and highly capitalized) startups have gone down in flames. It’s always the same story: overpromise, underdeliver. These are companies backed by hundreds of millions of venture dollars, who have created incredibly skilled teams, and yet, their product either isn’t value, unsustainable, or dysfunctional.

The common theme is that these startups are really good at sales—at convincing people of a product’s value. But they’re less adept at listening, co-creation, and doing the work to actually uncover and deliver value. So they sell something that sounds good but doesn’t actually solve a meaningful problem. Basically, they over-index on sales and underthink their product.

Discovering value is really hard. People tell you all sorts of things, but if we were simply to build a product that addresses what people tell us they want, we’d have very fast horses and no cars. Value discovery involves lots of translation and deep analysis—an inquiry into the question behind the question, or the intent behind the suggestion.

There’s a line to toe here: products are just as easy to overthink as underthink. If you’re too dogmatic about your product, you fall victim to the aforementioned overpromise trap. If you’re too open and flexible, you end up running in circles. A good rule that I’m still learning: fall in love with the problem you’re solving, not the solution you’ve built. The best early startups are held together with duct tape. Providing value—and solving problems—doesn’t have to be pretty. It just has to work.

the iteration game

Iteration is also extremely difficult. After spending time and energy and money building something that just isn’t valuable, it’s hard to ditch it. The sunk cost fallacy has a huge effect on proper iteration, so a lot of companies keep burning resources (and energy) in the wrong direction. Good iteration requires a ton of self awareness and very often results in damaged egos. You have to get out of your own way, remove your biases, and see things as objectively as possible.

The incubation period for a truly value product by my estimation is measured in years, not months; in iteration as well as insistence. Every time I’ve read into an overnight sensation, I find a long lead-up of failed businesses, years of zero revenue, and lots of pivots. Startups typically find the magical product-market fit after 4 years, and founders find success after 4 attempts.

Most people run out of steam (or capital) within only 1-2 years. It’s easy to see why. Last year, after pivoting into the people analytics space and building a product that received strong initial signals from customers, we just couldn’t get numbers up. Each (highly segmented) customer was asking for a slightly different set of functionality for a slightly different use case. We could not figure out a common denominator.

local minima

In the deepest throes of it last fall, we very nearly quit by way of an acqui-hire offer. A lot of people have recognized our ability as a product team, and an acquisition looks good on a resume. Plus, money was on the table. But one of our advisors, Nafis, brought us down to earth: “look, you guys know you want to be founders. You’re 22 years old, you don’t have expenses, you don’t have kids. You haven’t even given it a real try - so what if it fails? This is the cheapest and most valuable time to learn for you guys.”

He was right. I had begun to compare myself with a lot of people in my life who were making an easy 6-figures at consulting, banking, private equity, or product-focused jobs. Those jobs came with a clear pathway and clear indicators of success. I knew my earning potential, and knew that I was hilariously far from it. Success in startups is ambiguous - years of underpaid toil for a 90% chance of failure. And yet I’d turned down job offers in consulting, product marketing, VC, and innovation without hesitation.

signal identification is subconscious.

The Helm team took a break over winter. When we came back in January, like magic, everything became clear. By sleeping on it, we’d managed to parse the signal from the noise of the past year. The intention behind the insights we’d collected suddenly became obvious, and we knew the problem we needed to solve: disconnect.

Behind every great resignation article and retention metric is a core human truth: we desire belonging. We want to feel part of a community. Our ability to construct massive, functional communities is our differentiator from other species. If we do not feel part of something—if we feel disconnected from it—then it has no value to us.

It’s funny - with Helm, we’d gotten close to solving it before. Or at least, we’d built a product that solved for the problem of disconnect without realizing it. Now, it’s crystal clear and extremely simple: software that connects new hires with mentors, collaborators, and friends during the remote onboarding process. The result is both tangible and immeasurable: new relationships across a remote company (which drive retention, knowledge sharing, innovation, etc) and the feeling of being welcomed to a community.

(worth noting: we check 3 of the 4 boxes that define the typical gen z startup: community, vibes, and gradients. all that’s missing is web3.)

you can thank the TSA for the grain

making it work

We haven’t taken on major investment yet. Investment is a very expensive way to buy time to iterate and (hopefully) find value. Realistically, it imposes incredible pressure, clouding an already unclear process. Founders often take investment as a signal for value, but actually, investors are very rarely the customers of the company they invest in. And early rounds are entirely speculative, where most investors wait for someone else to make the first move.

We also haven’t needed to take on major investment yet. We will eventually. But for now, half of us are in school (on a part-time basis), and the other half support ourselves with part-time jobs. I do some consulting and education work with a wonderful initiative called the Hagedorn Legacy Foundation. I’ve worked with them since my first year of school, and in addition to paying the bills and affording extreme flexibility, it’s hugely fulfilling work.

skin in the game

And recently, with a couple old friends, we’ve started taking on 0→1 product development projects under the name Relay. This is exciting—we’re all naturally product-minded people, and within our friend group, we’ve built a staggering amount of product that has delivered on value. As a bunch of early founders, we’ve also learned to be brutally honest with product.

We think we can take this to expertise to early-stage ‘specialist’ founders who have incredibly deep subject matter expertise, some funding, and no product. Essentially, we’re acting as fractional CTOs or product managers, not only building but developing strategy as long-term partners. In exchange, we’re charging a fair rate while retaining some long-term stake (think RSAs or advisory shares). The big idea: skin in the game.

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Expect some exciting Helm updates soon. Also, Relay has started with its first client!

Last week, I switched my winter tires for my summer set. Yesterday it snowed. Timing is a weird thing, and things rarely seem synchronized. For a while, nothing seems to happen, and then it’s everything at once. Cheers to the week ahead!