28 Successful Founders Share Their Advice on How To Start a Startup
A journey of a thousand miles begins with a single step.
There are few journeys in the world that are as rewarding and interesting as that of an entrepreneur. Yet there is nothing more daunting than that first step.
It’s the one where most people falter, because for all the information out there on how to do a successful product launch or how to grow your email list, there is strangely very little information out there on how to start a startup.
I suspect one reason many people don’t become entrepreneurs is that they just don’t know where to begin, what that crucial first step is.
What we often forget is that the most successful entrepreneurs in the world all started out the same way. They didn’t know what the first step was or what they had to do, but they all managed to take it and become the amazing success stories they are today.
So we asked 28 successful founders from all types of industries and niches to give their advice on how to start a startup. We asked them these three questions:
- How’d you come up with the idea for your startup?
- What was the first step you took to build your company?
- What advice would you give to the younger version of you?
We hope you thoroughly enjoy their inspiring responses and nuggets of wisdom as much as we did, as each person gives their unique take on this tricky subject.
Shaun Neff, Founder and CEO of Neff
It started with passion. I grew up surfing, skating and snowboarding and my dream when I was older was to have a lifestyle brand such as the ones I loved and wore in high school.
I started selling t-shirts but found a niche in headwear that allowed me to go around the apparel contracts and sponsor the biggest athletes in the world in a category that was being overlooked. That was the little opening I saw in a crowded market and I used that as a starting block to build a global brand.
The first thing I did was hustle. I knew my product was not better than what was out there. I just sold the dream and vision I saw in my head and convinced others to jump on the journey.
Dream Big and follow your dream every single day until you are living the dream every day.
Focus on building the smallest, lightest thing you can so that you can reach customers as quickly as possible, getting feedback (and revenue!). We launched with four cars.
The reservation you made online had no real connection to the car. Anyone who owned an access card from our supplier could unlock the car door. The keys were dangling from the steering column. Anyone could have broken into the car and started the car. Members would fill out a paper log we left in the glove box: start and stop times; start and stop odometer readings.
These risks were actually minimal. Who would ever think about trying their office door proximity card to open these four cars? Who would ever look so closely to see car keys dangling? Within six months, our technology caught up and only the right person could open the right car at the right time.
Startups are really hard. Every successful one had terrible hurdles and setbacks that they had to overcome. These challenges are the norm and not unique to you and your startup.
Nathan Chan, Founder and CEO of Foundr
Foundr began because I saw a gap in the market. There wasn’t a digital magazine producing content for young aspiring and novice-stage entrepreneurs & startup founders, and I wanted to fill that.
My first step in starting Foundr was placing a financial wager on myself. To start Foundr Magazine, it required publishing software to produce the magazine and app. I placed $2,000 on the back of my personal card to start the app. This was money I didn’t have and also money I definitely didn’t want to waste.
My advice to my younger self? Party more, travel more, and stop worrying if things will work out or not.
Leila Janah, Founder and CEO of Sama
In 2005, I was working in India for an American management consulting firm at a large call center. One day, I met a young man who I learned commuted to the center from Dharavi, the infamous slum depicted in the film Slumdog Millionaire, and I was shocked. Here was someone capable of taking calls for British Airways who was living in a cholera-infested slum. I couldn’t help but wonder, how many more were like him?
At the time, I was reading Thomas Friedman’s book, The World Is Flat, and I had an epiphany: If outsourcing could generate billions of dollars for a few Indian and Chinese entrepreneurs, why couldn’t we use it to send a few dollars to the billions of poor people who need it most?
Soon after, in September 2008, I quit my New York consulting job and moved to Palo Alto to launch a social enterprise nonprofit called Samasource.
I love reflecting on the early days because there I was at 25 years old, sleeping on a friend’s futon, eating Top Ramen (a mentor of mine actually sent me $20 a month via PayPal for what he called a “Protein Fund”), trying to convince Silicon Valley investors to give me money for this bold idea I had of giving work to marginalized people as a means to solve global poverty.
Fast forward to today, Samasource has moved over 30,000 people over the poverty line in East Africa, India, and Haiti. We recently opened our first Samasource-owned work center in Nairobi and are already looking at expansion plans.
Alexis Ohanian, Co-Founder of Reddit
Y Combinator rejected our original idea and said they’d invest in us as long as we built for the browser (our first pitch was a mobile product, in 2005) and solved a problem we had every morning. Reddit was the result of that—not having one place to find out what was new and interesting about the things we cared about.
If I could go back into the past, I’d tell myself to keep on programming!
Darrell Wade, Co-Founder and CEO of Intrepid Travel
It was a long time ago now, way before there was any method or science to startups. Essentially, I was a very keen traveler who couldn’t stand the idea of going back to a conventional job! The question was, could I make a business out of the way I loved to travel?
A friend and I saw a gap in the marketplace between organized tours (very boring, but efficient from a time perspective) and adventurous backpacking (fantastic fun but time consuming). We hit on the idea of small groups, experienced leaders, and off-the-beaten-path itineraries. Intrepid was born and I guess the rest is history!
We did a paper-based MVP (though I’m sure the term didn’t exist then!) of what a trip would look like, rough costs, and what we thought we could charge. We ran it past a few people who understood the travel industry and should know if it would work. They all said we’d fail. Having never been one for market research anyway, we pressed ahead and launched anyway. We got a few sales, validated the model, invested every cent we could scrounge up, and then went hungry for a while! It certainly was not an overnight success, but we took 47 travelers to Thailand in our first year and that was just enough for us to have a second year!
This year we’ll carry over 250,000 travelers to about 120 countries. The secret to success—if there is one—is to have a good idea in the first place and then keep testing, iterating, and retesting EVERYTHING you do until you hit on the mix of marketing, distribution, product, pricing, technology and so on that works.
Melanie Perkins, Co-Founder and CEO of Canva
The best piece of advice I can give is to just get started. If I realized how much I would need to know before I started, I probably would have been too terrified to get going. But I’m a big believer of just-in-time learning, and we’ve learned a lot as Canva grew, and we’ll continue to keep learning as we grow.
Tan Hooi Ling, Co-Founder of Grab
I was never the type who grew up dreaming or striving to be an entrepreneur. Yet, somehow, I found myself passionately discussing potential ways to solve Malaysia’s taxi woes with my co-founder, Anthony Tan, a few years back. Idealistic beliefs and convictions led us to start MyTeksi in 2012. For those of you who are not familiar with the taxi situation in Malaysia, Googling “worst taxis in the world” can provide a glimpse.
I was personally often afraid to take taxis. I worried about getting into dingy beat-up cars with drivers who were often rude, unsafe, or would try to cheat you. Knowing this was a problem our families and friends struggled with too, we ended up developing the mobile application & technology-driven service that became MyTeksi, GrabTaxi, and now Grab. Our services help people book taxis, cars, bikes and delivery services in a speedy, efficient and safe way.
Eight in 10 women in developing Southeast Asian countries now find taking a taxi safer with Grab. Average taxi driver incomes have increased anywhere from 30 to 300 percent among our drivers across the region. I’ve also heard many personal stories from women, as well as drivers, who try to hold back their tears as they share how thankful they are for the impact Grab has brought to their lives.
It’s extremely rewarding to know that we’re able to fulfil the mission we started the company for. And even more so when we’re able to attract other talented and like-minded individuals who share this passion with us.
Eric Siu, CEO of Single Grain and Growth Everywhere
I began by solving my own pain points. It’s always best to become an expert in an area, find a pain point and go after it because you have a better idea of where to go.
The first step to my journey was a little different. I ended up taking over a company and then used the profits to cash flow my new startup.
My advice to all young entrepreneurs out there, not just me, would be: Start earlier. It’s never too early.
David Cancel, CEO of Drift
There’s one thing that my co-founder Elias and I would keep coming back to: sales and marketing are changing. Customers aren’t sold to anymore—they buy.
Information is free now, so businesses are no longer in control of the selling process. As a result, selling has become much more about truly understanding a customer’s problems and needs. So we wanted to build tools that make it easier for businesses to talk to their customers. We want to help businesses stop treating people like leads and start treating them like people.
Janine Allis, Founder of Boost Juice, Executive Director of Retail Zoo
Like most good ideas, they normally start with “wouldn’t it be good if.” For me, the end of that sentence said, “there was a business out there that made being healthy easy.” You need a curious mind to keep your eyes and ears open for ideas.
First step is always the Want, then comes the Idea, then the plan (with numbers), then the deep breath as you jump off the entrepreneurial cliff and finally you hang on and go for the ride. The ride is like a rollercoaster. Seriously scary with huge ups and equally scary downs. But who doesn’t want the rollercoaster ride?
So what would I tell my younger self?
The first thing is to have fun and lots of it in your 20s! You have a sense of adventure and risk-taking that seems to reduce as the years go on. It’s in your 20s and 30s when you have the biggest appetite for risk, so use it! You are also young enough to fix it if you mess up.
I would tell the young Janine to sharpen her “bullshit person” radar, and that not all people who seem to be nice are always so. Always plan for the worst-case scenario. Drop the plan in the bottom drawer hoping you never have to see it again, but feel confident knowing it’s there. Avoid doing business with friends if you want to keep them as friends. When things go well, remember to celebrate success and recognize the people who helped you achieve it. Don’t take money from your parents because spending money you have earned is so much sweeter.
In business, you need to be courageous. Don’t be that person who was too afraid to jump off the entrepreneurial cliff. If you are not scared, then your goals are not big enough. Reach for the sky and whenever you reach your goal, set another one bigger and bolder.
James Beshara, Co-Founder and CEO of Tilt
I saw a way to effect massive, important change in the world with simple software that puts the power of collective action and shared resources in the palm of your hand, and I have pursued that idea relentlessly for the last 6+ years.
In 2012, I built the Tilt platform to give people an easy and highly social way to organize and collaborate financially, whether it’s renting a boat with friends, a tailgate for a big game, bringing the Chainsmokers to your campus, or protecting a community from rising crime, Tilt was built to power it all.
To do anything of consequence, you’ve got to have both trust and a network. Everything else can come from that. Investment, refinement of an idea, co-founders, first recruits, all can come from building trust and a network. And one is useless without the other. So, even at a young age, start proactively investing in both.
Dan Norris, Founder of 7 Day Startup, author of Content Machine
For me, I just thought about what problems I knew I could solve for people and pitched it in a way that addressed as many objections as I could think of (fixed price, 24/7 delivery, unlimited jobs).
Starting was easy, all I did was email my list and pointed them to the payment button. From there it just grew.
One thing that’s important to keep in mind as an entrepreneur is that if it’s not working, be honest with yourself and try something different.
Morgan Hermand-Waiche, Founder & CEO of Adore Me
Like in every good story—there’s a girl. My girlfriend’s birthday was coming up, and I wanted to get her something nice. As a French guy, I immediately thought of lingerie. I looked online and in stores and quickly found that fashionable lingerie was way outside my budget! The bras alone were expensive, so there was no way I could afford a full set of bra and panties. Anything that I could actually afford was outdated, of poor quality, and in a limited size range. I couldn’t picture my girlfriend wearing any of it.
I realized that if I was facing this problem during one shopping session, others must be facing this problem all the time. That’s when I decided to look deeper into the US lingerie market: 40% of the market was dominated by a single player that was rolling over the costs of hundreds of prime retail locations to its customers, with even more costs online with high shipping and return fees. New collections were launched only four times a year and the newest, sexiest, most fashionable items were available only to women at a very limited size range.
Rob Walling, Co-Founder of Drip
My first step was to find 10 people willing to pay my asking price (at the time it was $99/month). Once I had verbal commitments from 10 people who wanted Drip, we put up a landing page and started building an interest list, and broke ground on the code.
James Crawford, Co-Founder and Managing Director of Beanhunter
One of our co-founders used to travel a lot with work and was frustrated that he could never find good coffee in new cities or areas. He would often spend his evenings crawling online forums and local papers for the best places to drink great coffee for the next day.
He came back from one of his trips and said, “There just needs to be an app that shows me where great coffee is and allows people to share these destinations.” There wasn’t, so we decided to build it.
When we started building Beanhunter, we had no real plan to turn into a business, rather we were just wanting to solve a problem. We had some ads on the site to cover our server costs but other than that the goal at the time was to build a useful product.
Validate the idea as quick as possible and “just do it.” Do your planning and testing up front before spending much, if any, money.
Rand Fishkin, Wizard of Moz
We had built some tools for our consulting business, and decided to make them available via a Paypal subscription wall. It took off far more than we were expecting, and we decided to keep pursuing it. Moz was really an unplanned startup in nearly every way.
In the very early days, when we were consultants, we meandered through finding clients and projects and ways to attract them. For all startups starting out, it’s a lot of experimentation, unsophistication, and credit card debt.
Benny Hsu, Blogger, Podcaster, & Online Entrepreneur at Get Busy Living
The very first thing I did was purchase a basic online course to learn how to get started.
Sure I could have gone to Google and looked for free info, but I wanted to learn from someone who was already successful. It was less than $50, so it was a no brainer for me to pay to have all the info I needed in one place. It helped because I had no idea how to sell t-shirts nor how to use Facebook advertising. I just wanted to learn enough to get started.
If I could give any advice to my younger self I’d tell him to stop wasting time searching for that perfect business idea in your mind. Instead of reading books, taking online tests, and pondering ideas to see which one is the perfect idea for me, go and try it out. It doesn’t need to be a full commitment. Just try it out for yourself in the simplest way possible so you have an idea if you like it or not. It is better than doing nothing and hoping that perfect business idea will suddenly come to you.
Eugene Woo, Founder and CEO of Venngage
My previous startup was in the same space (infographics) and we had some customers ask us for an infographic tool that was more flexible and simple.
We got a contract to do a custom development for a big client who wanted it. So we got paid for the first version of Venngage.
Don’t listen to so called experts and believe in your gut.
Vishen Lakhiani, Founder and CEO of Mindvalley
Nelson Mandela had said that one of the best ways to change the world is to change education and so I thought, “Well, if I could start any company, a great company to start would be a company in education, specifically in meditation.” And that’s how Mindvalley started.
First thing I did was hire a web developer in Bangsa. I was in New York at that time and this was a friend I had known from college and from high school in Malaysia. Paid him 2,000 Ringgit to build our first website. For 2,000 ringgit we started. I managed to become profitable after month three and Mindvalley has been taking off ever since then.
Be very careful with whom you share equity. Your equity is your future wealth. Do not give it away too freely. Do not underestimate your own abilities.
Chris Strode, Founder and Chief Product Officer of Invoice2go
The idea for Invoice2go came about 10 years ago when I was working as a freelance software developer for a large investment bank. The first thing I needed to do to get paid was send an invoice, but when I looked for a simple way to do this, all I found was complicated accounting software.
Coming from a family of small business owners, I knew I wasn’t the only one who didn’t want to wrap my head around a full accounting package just to send an invoice. That’s when I set out to build Invoice2Go. The tool that I wanted to use, and that I knew every other small business owner would want to use.
What I’d tell myself, and every other early entrepreneur out there, is to bootstrap your startup for as long as possible. Founders are often eager to raise funding and take their businesses to the next level, but if you can build a profitable business on your own, you’ll be better positioned to have a favorable conversation with VCs when the time is right. Focus on getting your product right where you want it for your users, and grow it from there.
Kate Morris, CEO and Founder of Adore Beauty
I started Adore Beauty out of a garage in Melbourne in 1999 when I was just 21 years old. While I was in college I was working a job on the cosmetics counters at my local department store. I came to realize that access to the best beauty brands were only available in major cities, and many of the women I met found shopping for beauty products unpleasant, often feeling pressured into purchasing by the classically pushy saleswoman.
Despite this being a time when people were suspicious of purchasing such personal products online, and there being no such thing as broadband internet, I was inspired to form an online store that would solve both of these problems simultaneously, and so I founded Australia’s first beauty e-commerce site.
My next step was to work out what the MVP needed to look like, and what was the smallest amount of money I needed to spend to get it off the ground. Once I had this framework and the numbers on paper, the next step was to source the money (which was generously loaned by my boyfriend’s dad). The rest is history!
I’m happy with all of the mistakes I made when I was younger as they led me to where I am now. Mistakes are a learning experience and in some ways I wouldn’t want to prevent them. However, I would tell my younger self to think a little bit bigger and be a bit more confident. There were some key parts in the growth of my business where I thought I maybe left it a little too long before taking a big, aggressive step. If I had my time again I would have gone a lot harder a lot sooner. But hindsight is a beautiful thing!
Georgina Nelson, Founder and CEO of truRating
I kept seeing the same problem coming up from several different sides—companies were desperate to hear from their customers but on average heard from under 1%, and consumers wanted to have their voices heard, but didn’t want to answer a 20-question survey about their salary, lifestyle choices, etc., just to have a say. Consumers were also shouting out for online reviews and ratings, but couldn’t really trust what they read, as the sites were either unrepresentative or could be easily gamed.
I had the idea that if a quick and easy survey question was available on the payment terminal, then businesses would gather information from paying customers and customers would be reassured of the validity of that feedback on a new comparison website … and truRating was born!
I had no idea at the beginning whether my dream could actually become a reality, or would make any money, so the very first thing I did was walk the streets and speak to those people who might buy the truRating product. At the time, I had my baby daughter, who was just a few months old, and my dad would push her around in her stroller on the streets outside while I went into local restaurants and shops to see if they had five minutes to chat.
After we had proven that it was technically possible, I reached out for investment.
Nick Molnar, Co-Founder and CEO of Afterpay
It’s often said that the best entrepreneurial ideas are simply about solving a problem. The Afterpay model was built around helping my online jewelry business sell more jewelry. Fine jewelry is a tough category, especially for online only, and customers were saying they would like a bit of time to pay for their purchases, but didn’t want to wait to get their pieces. I saw some online jewelers doing this in the US and thought, if this solution doesn’t exist in Australia, I’ll build it myself. And that’s how Afterpay started.
I would say to “young Nick” a few simple things. Work hard, seek contribution, play hard for success, but don’t forget the big things that matter. So, while I have made mistakes—we all do—I have a beautiful wife and amazing parents and that makes me happy and proud. The young Nick might not have always listened to the older Nick, but in most cases he has, and he is loving the journey.
Roland Tam, Co-Founder of Spacer
I started Spacer after a recent trip to Silicon Valley and New York with Investors Org, where I sat through a number of sharing economy presentations across a range of verticals. Having become addicted to Uber and Airbnb, I could really see the value of collaborative consumption and this is how Spacer concept was formed.
I am fortunate in that I had a successful business that I had sold previously, and a network of angel investors who were happy to back me in my new venture. We developed a MVP product via a SaaS provider in Silicon Valley, and it all grew from there.
Don’t be afraid to make mistakes, because this is the only way you learn. Most mistakes are not terminal in the grand scheme of your business, and so long as you don’t make the same mistake twice, the business will be better for it.
John Bush, Co-Founder of Easyshare
Like most millennials, I spent a portion of my 20s living in a shared house. I was often frustrated about chasing my housemates for rent and bills, and this was the seed for the idea behind Easyshare. I thought an easier way to manage splitting and paying household expenses would exist, however when I went searching I couldn’t find one. This prompted me to embark on the journey of creating one.
Advice I’d give to my younger self would be to spend some time in your chosen career to develop some core skills and more importantly, some self-awareness. The self-awareness will give you a really good understanding of your strengths, weaknesses, and the type of people you will need to surround yourself with to fill the holes in your weaknesses and complement your strengths.
Nancy Lublin, Founder and CEO of Crisis Text Line
The first thing I did when building Crisis Text Line was hire a CTO and Chief Data Scientist.
Advice to my younger self: Don’t go to law school (or grad school). You’ll learn everything you need to know by doing it.
Polina Raygorodskaya, Co-Founder and CEO of Wanderu
The idea for Wanderu was born out of my own frustration of not having one specific place online where I could find and compare all available bus and train options for traveling between any two points in the US. There are more bus companies than airlines traveling between major cities and, only a couple years ago, I had to visit every carrier’s own website and manually compare options to find the one that best fit my schedule. I realized I shouldn’t have to do all that every time I needed to go somewhere.
The first thing that my co-founder and I did when we set out on creating Wanderu was familiarize ourselves with the ground travel industry. We realized that, to create a truly innovative and efficient product, we had to be very well versed in the ins and outs of the bus and train business.
We bootstrapped the business for over a year. After all, to get investors to consider your venture, you have to prove to them that the business is something enough people would be interested in using, that you can get the right partners on board, and that it can be scaled.
If I could give my younger self one piece of advice, it would be to not be afraid of failure. Not everything you put your hands on is going to work right away. In fact, if you don’t make mistakes, there is no way for you to learn, improve and grow, and become a better entrepreneur.
“How do I get started?”
It’s one of the most common questions we get here at Foundr, and for good reason. Taking that first step can be so intimidating. For me, one of the most gratifying things about gathering up this advice—aside from the wide-ranging gold nuggets of wisdom they offered—was hearing from so many that they just had to do it—just take the leap.
More than a few of them acknowledged it was a little scary, or that they wished they’d started earlier. But they ultimately stepped into the fray, and their passions for their projects and willingness to take the risks should be an inspiration to all of us!
What about you all? Any words of wisdom about getting the ball rolling? Are you in a position where you’re just about to kick something off? Let us know below!