Evolution of Sales

In my own career, I’ve watched this long arc of sales play out on a smaller, very personal scale. Working with my dad in his small business, I saw how carefully he studied his customers: what they asked for, what they hesitated over, and what they lit up about, long before any data dashboard could quantify those reactions. We would travel across the country to discover products that were undervalued or poorly marketed, items with great “taste” or quality but weak positioning and then reimagine them with clearer branding, better packaging, and a sharper identity so they instantly made sense to our audience. That process felt old-fashioned and hands-on, yet it mirrored the same pattern that has repeated throughout history: understand people, find the overlooked gem, then make it obvious why it matters.

Today, in venture capital, I see the very same dynamics in a different arena. Many startups are building strong products or technologies, but they remain underappreciated in certain markets or demographics because their story is vague, their brand indistinct, or their positioning misaligned with how customers actually think and buy. The role of a venture firm, at its best, is to recognize those companies early, much like a merchant spotting a promising product in a crowded bazaar and help them refine their identity, clarify their narrative, and reach the right audience. When that happens, markets start to value these companies more accurately, and the “sale” shifts from pushing a product to simply revealing its true worth.

What fascinates me is how, despite the leap from cattle brands and guild marks to trademarks, logos, and sophisticated digital campaigns, the underlying principles have stayed remarkably stable. Whether you’re selling spices in an ancient market, consumer goods in a department store, or equity in a startup, three elements keep showing up: a distinct identity people can recognize, a simple and intuitive way to understand the offering, and a “taste of the future” that lets the audience imagine how their life or business will be better. 

Technology changes the channels, physical storefronts, websites, social media, venture pitch decks, but the human psychology beneath the sale barely moves.

Maybe the most interesting part of this journey is how these moments don’t stand alone, they move in circles. The evenings in my dad’s shop, watching him read a customer’s face, quietly trained the same muscles I use in every conversation today: really listening, noticing what people don’t say out loud, sensing what they might need next. Lessons from dusty shelves, long train rides, and chance encounters with overlooked products resurface years later in new jobs, new cities, and new relationships, just wearing different clothes. It often feels random while you’re in it, but over time the experiences rhyme; skills you picked up for one chapter suddenly become the missing piece in another. 

As Steve Jobs said, you can’t connect the dots looking forward, you only see the pattern in hindsight, yet those dots of curiosity, observation, and selling in different stages of life end up forming a single, surprisingly coherent arc of who you are becoming.