Lessons from an Immigrant Entrepreneur’s Second Act

"The good? There’s so much to learn. The bad? There’s so much to unlearn."

When Aashni moved to Canada to school many years ago, she was sure of one thing: she wanted to work in tech and then use all she had learned while working to launch a startup.

So, after graduation, she spent a few years working for software companies like Cash App to build the skills necessary to run her own business.

And just about when COVID barrelled into our lives, Aashni jumped headfirst into the entrepreneurial world.

“I launched my first startup, and it failed,” Aashni says, with light laughter that suggests a hard-earned resilience. “But I learned a lot.” 

Her biggest takeaway from that experience? Validate your startup idea first. Ensure customers are eager to open their wallets for what you’re offering.  

Now on her second startup, Aashni believes the experience she’s accumulated over the years has guided her through the often challenging but occasionally rewarding entrepreneurship journey.

We sat down with her to learn what it takes to run a business as an immigrant. Here’s what she said.

[Editor’s note: This conversation has been condensed for clarity]

What has been the most surprising part of entrepreneurship?

The good? There’s so much to learn. The bad? There’s so much to unlearn.

Haha. Say more.

Let’s start with the unlearning bit.

As a developer, I'd been taught to write tests and write all these different use cases for the things I built. But as a start-up founder, I don't have [the time or the bandwidth] to build everything yet. I’ve noticed that I have to be choosy about how I spend my time because there are always so many things to do simultaneously. So, being an entrepreneur has been unlearning my base programming.

Interesting. And the learning bit?

I’ve had to learn how to sell. As an engineer, I can build anything. But selling it is hard, and it's not a skill I'm good at. I have to learn sales because I’ve never done it before. 

I’m learning enough to help guide and lead the team. But I know I'll hire someone to take over that part in three to six months. 

Again, as a founder, I need to pick where I focus. I need to know the basics of sales, but I shouldn't spend all my time on sales when I could hire someone and focus on other parts of the company.

Curious: Do you still have time for your first love, which is writing code?

I have to be a lot stricter with how I use my time, and I have a way of breaking down my day and schedule. I'm bootstrapping rather than raising money, and because of that, I need to keep a close eye on my finances. As a result, I do some contract work on the side. 

A typical day involves allocating a few hours to focus on the contract work and meeting those requirements and deliverables. Then, I spend the rest of my time working on my company, HypeDocs.  

I try to take time off between 6-9 p.m. or 7-10 p.m. to go for a walk or talk to friends—just to take a break. I should add that I’m absolutely fine with working on weekends, but I’m also okay with taking a break, especially on days when I feel off, during the week to balance things out. 

Whew!

Let’s say I wanted to start a business. How would you prompt my thinking? How would you set me up for success? 

The first step is always having an idea but also having ways to validate that idea. So, instead of spotting a problem and coming up with a solution, a better approach might be asking people questions to understand how they deal with it. After gathering that information, you’ll have a nuanced perspective and better solutions. The Mom’s Test by Rob Fitzpatrick is a book I highly recommend on this topic. 

Okay, I’m taking notes.

Once you understand a problem space well, you can apply that knowledge in many different ways or find and build solutions for it. The next step is figuring out who's willing to pay for the solution.  

Wait, I feel like you’ve lost me here.

Okay, let’s call this “Starting a Business 101.”

The steps for succeeding would include something like this:

• Make the decision to start or have an idea. 

• Start talking to people and understand what problems they're facing with your chosen idea.

• Use this information to come up with some possible solutions.

• Build simple prototypes to test your idea and get feedback from an early stage. As you keep getting feedback, you'll validate your product that way.

• Start selling as soon as you can. 

Ah, Gotcha. Let me put you on the spot here: Give me a real-life example of how you’d do this.

Haha. Let’s see.

In February, I was trying to book a trip to Vancouver for July. Even though I was searching months in advance, the cheapest hotels I saw were just under an eye-popping $400 a night, which was way more than I was willing to spend. 

So, I thought: there are people who probably booked way in advance for July and now might be unable to make the trip. And the hotel likely won't refund them the hefty cancellation fee. 

What if, I mused, there was a way to play matchmaker?

I could test the idea of setting up a space where people desperate to cancel a reservation could transfer their reservation to other travelers on the hunt for a discounted stay. The next question is whether people will be willing to pay for this service and at what cost. Also, how do you monetize this service? A commission for each transaction?

You have my full, undivided attention.

However, even before getting to that point, you could ask a few people about the problem space you're working on. In this case, my problem is that hotels are crazy expensive, and I want to know how to book cheaper ones. 

I could talk to ten people and ask them how they book hotels. A simple question like “How do you find cheap places to stay?” would unlock many possibilities. 

As you start asking more questions, you'll potentially and hopefully see that there's a space that people don't want to book far in advance because if plans change and they cancel, they don't get a refund. People can't also afford hotel reservations if they're booking at the last minute. What if you could connect people who booked in advance and want to cancel with people willing to take over at a cheaper rate or whatever? 

The beauty here is that you don't have to build an entire app to test the theory. You could create a prototype, send it out to a few people, and post a few posts on TikTok or IG to see how people react. 

That's so impressive. Your mind seems wired to spot opportunities. How did you become the type of person to spot opportunities and develop the muscles to test the theories? How much is nature or nurture?

A little backstory: I come from an entrepreneurial family. 

Back home in Kenya, my family runs a few businesses. I grew up watching my dad run multiple businesses. I also spent several months interning at one or two of those businesses and in different roles. This means I've been taught to have an entrepreneurial mindset from a young age. The implication is that a lot of this is nurture.

However, this realization is interesting because the businesses we run in Kenya aren't tech businesses. They’re not even tech-enabled. They have very rudimentary processes. 

What's fun and interesting is that I'm taking all this knowledge I've grown up with and been surrounded by, adding it to the education I’ve received, and doing interesting things with it.

It shows.

I think this is also true for many immigrants who come to this country—they have all this outside knowledge and experience. The hustle culture is real in many other countries. At least, I know it's massive in Kenya, where I grew up. 

To answer your question, I was born with some percentage of this. Entrepreneurship is a family trait—it runs in our blood. Add this to my knowledge of how to build and develop products and how to evaluate which types of products are getting out there and becoming successful, and you can trace how I’m able to merge everything. 

Can I tell you a little secret, though?

Sure! I love secrets

My sister, who has a similar upbringing to me, is not interested in entrepreneurship. She doesn't want to run her own company or anything. She’s perfectly fine with working a 9-5. So, maybe we need to revisit the “entrepreneurship running in the blood” bit.

Hahaha.

Tell me: How do you deal with the disappointment of not seeing a product take off as you imagine?

You have to be honest with yourself. It's something I've had to learn. It also involves setting boundaries on how long you're willing and able to work on something, assessing yourself, and coming up with quick hypotheses. If that doesn't work, you'll move on to the next thing.

Another thing is having a community of people to talk to, like I do. You'll find that you're not alone, and everyone goes through this struggle. Most companies take years to figure out how to be successful and monetize. When you have a group of people cheering you on, it makes a difference. 

What would you do with your time if you had one million dollars and didn’t have to work?

I like to work on projects that positively impact the world. If money didn't matter, I'd spend my time on those. 

I'd also focus on ensuring that Hype Docs has a substantial positive impact—not just on the company paying for it but also on the individual users using the products. 

One thing that keeps me going with Hype Docs is that my passion for the solution comes from a real need that I've experienced and that other people have experienced. HypeDocs is a tool that helps managers gain better insights into their teams to support them better. It also helps team members track their accomplishments, which helps during their performance and one-on-one evaluation. 

I'm passionate about this because I've had poor and great managers, and the distinction between them is big. I’m positive that Hype Docs can help me and others who use it have much more control over their careers—and that's what keeps me going. 

I have these skills and knowledge and want to make sure I'm making a positive impact in the world with them. 

Inspiring! Thanks for chatting, Aashni.