The Startup Dream vs Reality: The Real Deal from Five Founders

What’s the life of a startup founder actually like?

Startups are glamorous. Cool. The dream career.

At least, that’s what many people seem to think.

But that caricature of owning a startup can ignore the reality. In this article, you’ll hear from five startup founders about four important skills in startup life.

We’ll discuss these skills, and then suggest a resource at the end to help you if you’re considering starting a startup.

Essential skills for founders

You probably know that founding a startup will be hard work. But you might not know that you’ll also have to become good at:

• Making decisions under uncertainty

• Becoming a generalist

• Managing unstructured work

• Maintaining mental and emotional flexibility

Making decisions under uncertainty

Decision-making is hard – partly because sometimes, it’s impossible to know if you made a good decision. Founders must find a way to become “okay” with the uncertainty.

“You should only run a startup if you LOVE ambiguity,” founder Katie Kirsch said. “You’re constantly making decisions, and you often don’t know if you made the right or wrong decision.” The world might give you feedback on your decision. Or it might not.

Katie’s coaching startup, lume, helps ambitious people solve the problem of uncertainty, by empowering clients (including founders) through coaching services.

Katie described the myriad decisions that she makes each day. Decisions about sales, operations, team building, pricing the product, and scaling the company. And because the company has never been run before, there’s no “roadmap” Katie can follow.

Decision-making without clear evidence

Even data-driven insights can be ambiguous, forcing founders to trust their instincts.

Shanee Benjamin reiterated how difficult it can be to make decisions without clear evidence. Her product is a dry shampoo for the African American community – a product that she created because she couldn’t find anything that suited her well.

But even when she solicits feedback from her active Instagram community, it’s hard to get clear answers. “I posted a poll to see what [the community] liked the most. But Instagram users didn’t give me a clear answer.” She’s tested multiple iterations of the shampoo – “but I’m not the only customer.”

She’ll have to make a decision, and she’ll have to sit with the ambiguity of never quite knowing whether it was right.

Becoming a generalist

Many founders are specialists—engineers, marketers, product designers. But to succeed, they often need to deal with many more aspects of the business, such as HR, taxes, and sales.

In short, if it needs to be done, you have to do it – and you have to figure out how.

Ryan Hughes, who was trained as a software engineer at Northeastern University, has had to learn a whole host of new skills. with a degree in software engineering. He runs a software consulting startup, Fan Pier Labs, and had to learn to negotiate contracts, and do taxes for a small business -- among other things.

“You’ve gotta learn as you go,” Ryan said. He had to learn to network and to delegate, including networking with potential clients and pulling in other dev shops.

Managing unstructured work

There’s always more work to do – and there’s no clear end goal. Prioritization and managing unstructured work is key. You must always be working on multiple things.

“There are always fires to put out,” said Jaime Paris Meseguer, founder of pet care startup Pronova. “You go to bed on a fire and you wake up on a fire.”

"Your plate has to be pretty big. You need to take on a lot of tasks at once, and focus on a subset of them at a time,” Jaime told us.

But identifying the right guiding questions to help you figure out an effective use of your time is KEY.

At this stage of his company, Jaime has identified the right questions to ask to help him prioritize his activities and effort. He asks two questions:

1. Does the activity prove the tech works?

2. Does this activity prove people will buy the product?

Of course, the two questions will differ for every founder, but learning to ask the right questions is key. Jaime identified an over-arching question to help him prioritize his work: “Does it make the boat go faster?”

Every founder must develop their own questions to guide them toward their goal.

Managing mental and emotional flexibility

Running a startup is hard.

You always feel “on”. You’re torn down by customers, and users, and other people.

That’s what Lucas Arfinengo – CEO of Daby – told us. He describes his company as, “Coursera meets Unidays.”

Lucas is passionate about what he’s building, and that passion is necessary to help him combat the mental toll. He thinks founders should consider what sacrifices they’re willing to make.

“Are you ready to make drastic sacrifices?” he asked, “I’ve lost a lot of friendships, sacrificed a lot of personal net worth—95% of my net worth as of now to bootstrap.”

Prepare before you plunge in

“DO YOUR RESEARCH,” Shanee Benjamin told us. “Before you go out there and create a product, interact with your community and target customers and how to make it better for them.”

Lucas told us: don’t assume that just because you build a product, your target market will care about it. “You have to be wary: you can’t take your assumptions without validating them.”

In other words, make sure there’s demand before you build.

One suggestion and one resource

Suggestion on decision-making

All of the founders we spoke with mentioned that one key factor in making good decisions is: getting advice from people you trust. (Katie’s company is built around this idea, among others!)

A supportive community of advisors and peers can be crucial to help you make good decisions. Often, your community will see possibilities you did not think were possible. Foster a community of peers, advisors, friends who you can go to when you need to bounce off ideas.

You can ask questions like:

1. “What is your process for making decisions in your day-to-day?”

2. “Walk me through a difficult decision you’ve made recently. What went well? What would you have done differently?”

This can help you recognize the range of decisions that are possible.

Resource to learn more about the startup journey

Realist Lab is a startup accelerator to help potential founders learn more about the startup journey.

Realist often accepts founders who are at the idea stage. Over a course of two months, Realist helps you think about customer discovery, idea validation, and the needs of your product.

As Shanee and Lucas noted, building a product is HARD. Realist aims to help you de-risk the earliest parts of the founder journey. You could even do it while you’re still employed full-time.

Disclosure: Christian does work for Realist and is shameless about encouraging potential founders to apply. Realist offers a variety of programming for idea-stage founders but does not guarantee any funding, venture or non-dilutive grants.

The program could help you crystallize how to build a product with market demand and you go after it firing on all cylinders. Or, after talking with potential users and investors, you determine that this might not be the right time.

You may benefit from knowing that you gathered more information -- and did so without spending 25K on an app with zero traction. If you’re not sure what or how to build, I would highly encourage looking into Realist Lab and other idea-stage accelerators.

Are you ready to embrace ambiguity, master a bunch of different skills, and make decisions on the fly? If you’re still feeling energized after reading this, reach out to a founder, join a startup event, or explore programs like Realist Lab to take your first step.

Was anything in this article helpful? If so, please let us know in the comments. Or, email trailblazingtwenties.substack.com.

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