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22 founders share the one factor they wished they’d identified earlier than beginning a business, Enterprise Insider

Being a founder isn’t just about getting funding and clients.
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  • Starting a company comes with all sorts of struggles. You have to find that perfect idea, get funding, and hit the ground running.
  • But beyond those known challenges, there can be surprises along the way. Here, 22 founders share their unexpected experiences – and what they wish they had known.
  • Many stressed the loneliness of being an entrepreneur – something that they didn’t expect – and how it can feel constantly uncomfortable to not know what’s coming next.
  • “Your first clients will lay the foundation of your business, message, and portfolio, so it’s worth passing up less-than-ideal opportunities to wait for the ones that match your target,” said Catalyst founder Sara Dahan.
  • Visit Business Insider’s homepage for more stories.

It’s no secret that starting a company is hard work: finding the one idea that inspires you enough to work on it full time, securing the funds you need to get started (or bootstrapping your way to profit), and signing your first clients or partners.

But most people who’ve ever even thought about entrepreneurship know about those hurdles.

It’s the unexpected hardships that tend to affect founders the most. After all, most people don’t tend to talk about things like the loneliness, the tough decisions, and the constant fear of the unknown that come with running your own shop – which makes it even tougher when you do experience them.

These seasoned founders are ready to share the surprising side effects that have accompanied their entrepreneur journeys. Here are their stories: the unforeseen lessons they learned, the advice they want you to know, and the inspiration that, although tough, starting a business can ultimately be the best decision you make.

1. Jessica Mendoza

Jessica Mendoza.
Courtesy of Jessica Mendoza

Founder and CEO, Monadd

What no one told me: You are going to need twice the amount of money you think you’ll need. The minute you think you have everything set up, someone will tell you the things you don’t have, and it’ll be up to you to make hard decisions on where to spend your money.

My advice to others: Do research and ask. I know how hard is to ask about money, but when you are going with all your might to fund and build the company of your dreams, then questions should not come as hesitations but rather be the place where clarity starts.

2. Jenny Thompson

Jenny Thompson.
Courtesy of Jenny Thompson

Founder and CEO, SafetyPin

What no one told me: That none of my “credits” transferred. While I thought my experience would help assure partners and investors, it seemed to make them think I was stale.

My advice to others: Do more legwork in advance than I did. Build your new network, get involved in another startup on the side to build your experience, and go to pitch nights/entrepreneur forums/etc. before taking the leap.

3. Miraya Berke

Miraya Berke.
Courtesy of Miraya Berke

Founder, Dessert Goals

What no one told me: I have been most surprised by how different every day is. Some days I’m on top of the world, meeting with people and feeling great, others I’m grinding away alone sending emails.

My advice to others: I would recommend to anyone who knows they need a structure to set it early on. I thought the routine would come over time but without making it my priority I still don’t have one.

4. Sara Dahan

Sara Dahan.
Courtesy of Sara Dahan

Founder and CEO, Catalyst

What no one told me: When I first started my consulting business, I was in the hustle mindset. I thought all paying clients were a good choice – but it’s not true!

My advice to others: Your first clients will lay the foundation of your business, message, and portfolio, so it’s worth passing up less-than-ideal opportunities to wait for the ones that match your target. Being reactive to offers will make you feel like you’re drowning, even if you’re getting lots of business.

5. Robyn Hounjet

Robyn Hounjet.
Courtesy of Robyn Hounjet

Founder and CEO, studio co.creative

What no one told me: It is impossible to build a thriving business without first doing your inner work; the health of your business is entirely dependent on your physical, spiritual, emotional, and mental health.

My advice to others: The entrepreneurial journey will unearth every story, pattern, and fear that you have – so it’s essential to create a self-love strategy that complements your business strategy.

6. Kaitlin Christine

Kaitlin Christine.
Courtesy of Kaitlin Christine

CEO and Founder, Gabbi

What no one told me: No one talks about how incredibly isolating it is to be an entrepreneur. You wake up alone, you work alone, go home alone, and go to bed alone just to do it all again the next day. In the early stages, the hardest part: You are a one-woman show.

My advice to others: There is a lot of “glamour” associated with being an entrepreneur of a startup. The truth is, it is not glamorous at all! I think this myth is such a mystery because of the rampant success many startups have had (such as Airbnb, Lyft, DropBox, etc.). My advice is to be just as intentional creating a community and tribe of fellow female entrepreneurs as you are with your business.

7. Dominique Mas

Dominique Mas.
Courtesy of Dominique Mas

Founder, coach, and speaker, Lead With A Twist

What no one told me: Everyone told me that it’s about who you know, not what you know, yet the most surprising thing to me was that so much of building my business would be dependent not only on my network but rather the act of giving to my network.

My advice to others: Seek a diverse community (like Dreamers // Doers) and be a giver: Offer your advice and expertise and others will reciprocate with theirs. It will propel your growth in every sense of the word: personal, professional, and business-wise.

8. Alexandria Carroll

Alexandria Carroll.
Courtesy of Alexandria Carroll

Founder and CEO, License to Drift

What no one told me: It took a while for me to break the habit of feeling like I had to have all these answers before I could ask for help.

My advice to others: I encourage other women to ask for help unabashedly and pay it forward as they build entrepreneurial expertise, so that we can all achieve our visions for the world.

9. Mimi Bishop

Mimi Bishop.
Courtesy of Mimi Bishop

Cofounder, The Resting Mind

What no one told me: The key to building a business is becoming comfortable with being uncomfortable every single day.

My advice to others: Think and envision the big, bold goals and go about it one new experience at a time. Be sure to take a moment and reflect on what you’ve achieved before moving on to the next challenge.

10. Jamie Lieberman

Jamie Lieberman.
Courtesy of Jamie Lieberman

Owner, Hashtag Legal

What no one told me: I presumed I would be excited and open to hiring staff when my business had grown enough. When the time came, I made excuses to avoid hiring and waited way too long.

My advice to others: Hire before you think you need to! Plan ahead and once you find the right person, you will be ready to hit the ground running.

11. Peyton Ladt Sterns

Peyton Ladt Sterns.
Courtesy of Peyton Ladt Sterns

Cofounder and CEO, Bashed

What no one told me: How lonely it can be. When you work for yourself, it’s up to you to put the keys in the ignition and start the engine every day, even when you’re not sure where you’re driving to.

My advice to others: Surround yourself with other people who are founding their own companies. Once I connected with a few other people in the startup world, we’d have coffee just to talk, vent, sometimes cry about how hard it can be to go on your own – but there was great comfort in knowing that I wasn’t actually alone, other brave souls were in it with me!

12. Kate Anderson

Kate Anderson.
Courtesy of Kate Anderson

Cofounder and operations, iFundWomen

What no one told me: It is critical to have a cofounder or cofounders you respect and who complement your work style. You cannot build a scaleable company in a vacuum and cannot achieve your fullest potential by working solo.

My advice to others: I hope that every female founder when starting her business is immediately seeking out a cofounder to help her scale and stay challenged. If you cannot find a cofounder, investing in a great coach or mentor can help substitute until you find someone who is the right fit.

13. Julia Olayanju

Julia Olayanju.
Courtesy of Julia Olayanju

CIO, GrubEasy Interactive Labs

What no one told me: I wish I knew how important networking is to running a successful business. I thought there were many factors to building and growing a business but did not pay much attention to building my network when I started out.

My advice to others: You cannot downplay the importance of building a strong network for a successful business.

14. Michal Levison

Michal Levison.
Courtesy of Michal Levison

Founder, Seasoned Moments

What no one told me: No one ever told me just how lonely it is to start a business. At the beginning, I was completely engrossed in the little details so I missed that I was doing everything by myself. Suddenly, I was overwhelmed with the solitude of it all – literally and figuratively.

My advice to others: Join one of the many communities now available to female founders. You can get everything from HR help to coaching to travel tips and friendships. The support is probably the most important aspect of these groups. There is no reason to go it alone anymore.

15. Lindsay Gordon

Lindsay Gordon.
Courtesy of Lindsay Gordon

Career coach, A Life of Options

What no one told me: The highs are way higher than any 9-to-5 I’ve had and the lows have been way lower than any 9-to-5 I’ve had.

My advice to others: Learn as much as you can about the true ups and downs of running your own business before you start, and surround yourself with great support to help you get through the hard moments – and celebrate the wonderful ones!

16. Naysa Mishler

Naysa Mishler.
Courtesy of Naysa Mishler

Cofounder and CEO, Everest Effect

What no one told me: You need talent to secure resources, and resources to secure talent.

My advice to others: You need to be an expert in your field, but also monitor other trends. As more industries converge, you start to see new opportunities, and resources and partnerships emerge-many of which can benefit companies large and small.

17. Shannon Emmerson

Shannon Emmerson.
Courtesy of Shannon Emmerson

President, Forge and Spark Media Ltd

What no one told me: The extent to which I’d feel like my business was me: flaws, values, abilities/inabilities, delusions, warts, and all. It’s an incredibly personal thing to own and grow a business that reflects who you are.

My advice to others: Let other agency owners know that you will be in full view as you grow your business, make hiring decisions, select clients, and focus your services. Be prepared to put it all out there.

18. Monica Rivera

Monica Rivera.
Courtesy of Monica Rivera


What no one told me: Starting a business can feel completely isolating at times. After a particularly grueling 13 hours of editing audio and feeling relieved and accomplished, no one in my family could relate to what I’d just done.

My advice to others: It’s common to hear that you’ll work harder as an entrepreneur than you do as an employee, but if you’re beginning your business by yourself, you’re a jack of all trades, wearing all the hats. This is exhilarating and exhausting, so my advice is to extend yourself grace because you truly are doing the best you can!

19. Keira Kotler

Keira Kotler.
Courtesy of Keira Kotler

Founder, Everviolet

What no one told me: No one prepared me for how generous and eager other people, even strangers, would be in support of my business. I have been overwhelmed by an outpouring of free advice, feedback, encouragement, and introductions that have made my life so much richer than it ever was before.

My advice to others: Don’t be afraid of being open and asking for help – there’s no shame in not knowing everything (who does?), and others really do want to help.

20. Ellie Hearne

Ellie Hearne.
Courtesy of Ellie Hearne

Founder and CEO, Pencil or Ink

What no one told me: If you don’t treat yourself like a serious and successful entrepreneur, no one will.

My advice to others: There’s more to starting a successful business than confidence and optimism – but they go a long way.

21. Marianna Sachse

Marianna Sachse.
Courtesy of Marianna Sachse

Founder, Jackalo

What no one told me: I’ve found that a culture of hiding your work and hoarding your skills – like a squirrel hoards nuts – does nothing for you. Rather, sharing knowledge and expertise with peers opens them up to do the same for you, and together you grow more.

My advice to others: When you put collaboration over competition, everyone wins. To help you get there, join networks where you can connect (in person or online) with entrepreneurs that share something with you: groups for women, minorities, or based on business type.

22. Jessica Gupta

Jessica Gupta.
Courtesy of Jessica Gupta

Founder and CEO, Taavi

What no one told me: It can be a really lonely experience. Creating a company out of an idea takes a lot of mental space, and not being able to calibrate the tougher times with a team can be hard.

My advice to others: Connect with people. It can be so nice to share your work with others.

Dreamers // Doers‘ mission is to increase the number of successful ventures launched by women. It consists of Collective, a high-impact community reaching over 25,000 women globally, and Onyx, a highly curated private members’ collective for value-driven female founders, trailblazers, and change-makers.

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