68 Entrepreneurs Share Their Biggest Challenges Growing a Startup

68 Entrepreneurs Share Their Biggest Challenges Growing a Startup

The biggest challenge is that most of the times you think that you don’t have resources.

You’d like to grow your team but you don’t have resources, you’d like to get national coverage but you have no budget to do what RedBull does, you’d like more customers but… you get it.

Solution: I’ve studied a lot what the most successful people do – having done interviews in TV/Events with Jeff Bezos, Steve Ballmer, Al Gore, Seth Godin, Tony Robbins and hundreds more – and I keep seeing common patterns.

The solution is always the same.

1) Complaining is not a strategy
2) “The defining factor is never resources, it’s resourcefulness”
3) Get smaller to get bigger

Here’s a personal example.

Few years ago I wanted to promote a new startup with zero budget and we came up with the idea of gathering together 1000 startups on an high speed train traveling from one city to another (sort of a hackaton on a train). Certainly a great marketing stunt, but very expensive to get a train only for you.

To solve the problem we’ve prepared everything in advance (contacting startups and experts, scripted the format for the 4 hours trip, got a pre ok from potential partners if the trip was going to happen) and with everyhing ready we’ve organized a meeting with managers of National Railways Company and they agreed to be the main partner and give us a train free of charge.

They got an innovative project with zero effort (and huge coverage). We got great media coverage and contacts we couldn’t ever had alone. Your ideas are your best resources 😉

Marco Montemagno, Marco Montemagno

Making a name for ourselves in a market dominated by big players was challenging. We found that the best way to build our brand was through a grassroots approach. We honed our voice and marketing efforts towards the community and built a strong relationship with them. We later relied on them when it came to fundraising, which we did through Kickstarter. Alone we were just a few people tackling a big problem, but with the help of the community we were able to make a dent!

Tom Giannattasio, Macaw

The first challenge was putting our team together. We needed people who were business-minded and who were passionate enough about what we were doing to work for peanuts for years until the money situation got more comfortable. Thankfully, we found the right people and we got there without ever having to have angel investors or do any serious fundraising.

The second challenge was getting over the idea that there would be a tipping point after which we’d be super successful, and instead getting used to the idea that it would be a slow build over a long time, but that that would be fine. We overcame that challenge by keeping a close watch on how our business was growing month by month and focusing on our successes while continuing to build.

Kevin Allison, Risk!

As an entrepreneur we all wear many hats, but as we start growing our business, it is very important to identify which one of those hats need to be turned over to others so we can scale the business. We built our business from day one in an always ON fashion but set clear expectations for customers on what and when to expect from us. Staying focused on what you offer and managing it well is key to growth.

Timo Selvaraj, SearchBlox

Keeping the customer service quality at an acceptable level is our biggest challenge. We do it with a combination of a decent help system, per-ticket customer feedback, net promotor score surveys, escalation plans for customers, pro-active fixes and manually replying to customers who aren’t happy. This is an ongoing challenge and we are always looking for ways to improve this.

Dan Norris, WPCurve

One of the biggest challenge I’ve faced is getting traction; I know, I’m not original, but this is the most acknowledged challenge of being a digital entrepreneur.

We engaged our 10k users, one by one, giving them support and helping them growing their businesses too. This is what we do (and I personally do it) every day.

Nicola Ballotta, wpXtreme

The biggest challenge I’ve faced while growing my business is managing the workload. As a solo founder it’s extremely difficult to take on and execute all of the responsibilities related to the business – it leads to extremely long word days, 7 day a week.

To overcome the workload challenges I’ve broken up every part of the business into separate roles that can be delegated to interns. As these tasks are executed I’ve also documented the processes in detail in order to create replicable and easy to follow systems for future team members.

Evona Niewiadomska, Undiscovered Kitchen

SummaList was launched as a premium service and the biggest challenge was to attract and grow the customer base. After a period of plateaued subscription rate, I’ve decided to change the business model and made the service free of charge. It took off immediately and we saw an impressive growth in new subscriptions.

Right now we’re working to introduce some premium features. We expect about 3-5% of our current subscribers to upgrade to a paid account and this will be enough for us to continue the project and release new features.

Mihai, SummaList

Challenges are a dime a dozen when you have a startup. Everything from constantly trying to get customers to managing the process is daunting, but by far the biggest challenge I’ve had is trying to do everything myself. It’s easy to forget that I can delegate tasks. Now by doing so, I’m able to free up my own time so I can focus on what really matters; growing my business and building relationships.

Steph Russell, Vizually

The biggest challenge we faced early on was talent and hiring. In the earliest stages of a business, the biggest investment made is often the employees, both from a monetary and trust standpoint. At the same time, it’s important to build a good team and sometimes time is of the essence.

To overcome this, our CEO, Alex, made hiring a number one priority for two months. That led to the hiring of myself as well as our CTO and some of the most talented interns I’ve ever met. It was a process of being very present at events, holding a ton of meetings, and not settling for anything less than complete assurance with the candidates. It was very time intensive, but the individuals and their work ethics quickly made up for time lost.

Jay Clouse, Tixers

One of the biggest challenges is maintaining your focus. It takes guts and a huge amount of discipline to say “no” to opportunities that come up, but because you’re resource-constrained it’s necessary for survival.

Sally Carson, Pinoccio

The greatest challenge I have faced as an edtech entrepreneur, specifically one that is working to integrate coding into the classroom, is encouraging educators, many who are not technically savvy in the strictest sense, to step outside of their comfort zone and learn alongside their students.

With Kodable, we are teaching young students the basics of computer programming, a concept that the vast majority of teachers are totally unfamiliar with, and requires more of a bottom-up learning process.

When teaching coding with Kodable, educators are forced to learn coding alongside their students, which can often be uncomfortable for them, so in order to combat this we spend a ton of time providing them with the tools to facilitate and make this a more comfortable process.

Recently we came out with Kodable Class, an app that we designed specifically for use by educators in the classroom that provides them with all the resources they need to both learn and teach the basics of computer programming to their students.

We designed an app that was aimed at teaching young students, and we were successful in doing that. However, what we realized along the way is that if we wanted Kodable to be sustainable, we would have to create an entire curriculum that helped to teach all the parties involved, including adults.

Jon Mattingly, Kodable

My interactive agency, Simple Focus, was using a spreadsheet to run our production meetings, but it was difficult to maintain. We decided to build Project List, which is a simple collaborative, transparent project management dashboard that would make updating the team easier for us and other teams, too.

While we have a lot of experience designing products for our clients, Project List was our first attempt at designing one from the ground up that we also had to market. We love the product that we’ve made (and so do our early users), but the biggest challenge has been marketing a brand new product without a built-in audience.

Marketing is hard.

Our solution has been to approach marketing Project List with the same principles we used to build it: patience, transparency, collaboration and a lot of hard work. So far, it’s paying off, and we’re seeing our audience grow little by little.

JD Graffam, Project List

As a solo founder with a full-time day job and family, actually launching and selling a software product within months instead of years has been one of my biggest challenges.

This was overcome by building WordPress plugins instead of a SaaS. Lack of MRR is made up for by generating sales and turning a profit much faster.

Phil Derksen, Stripe Checkout

Creating sales leads online in a way that lets poor leads remove themselves from my database — to self-filter. This results in fewer leads in my email database but allows personal “”touches”” for the leads worth touching.

The result: Revenue growth that scales.

Basically, I’m using using blogs and video (content marketing) to “”get discovered”” based on prospects’ pain or goals. I offer tips in a way that creates hunger for more tips, tricks & shortcuts.

For example, I write a 600 word blog leading readers to a 12 minute video. This creates hunger for more tips — in the form of a live online Clinic where I “”diagnose and treat”” a pain my prospects’ have. This live online Webinar leads to a low-cost “”first step”” product that brings customers into my world for up-selling (also, “”proves me out”” to larger corporate clients who need team training).

Jeff Molander, MakeSocialMediaSell

It’s incredible how much you need to pivot yourself, not just your products. Being all things to all people makes you successful when you’re small and starting out, but those same traits become a huge hinderance when you take on more staff. Learning management for a freelancer, learning leadership for a manager, those pivots don’t come naturally.

I was lucky enough to have some great people around me, people who could identify and communicate those things which hold the business back. And when it was me, they weren’t afraid to say it.

Murray Bunton, Agency

Since our team is comprised of engineers we didn’t have any issues getting the technology built—all of our focus has been on getting customers. For us, there hasn’t been a single golden bullet to get us the level of customer acquisition we want, but there are a few bronze bullets we’ve been working with:

– Word of mouth has been surprisingly strong, which I attribute to great support and asking for referrals.

– Google Adwords has been providing us a nice return, but is still too expensive to quickly pay itself off. Be prepared to invest the time into good ad copy and customized landing pages.

– Outbound sales facilitated with learning from our data has been very fruitful. For us, we learned that ~50% of customer base deal perform marketing services for clients, so, we built specific content for them.

Brian Sierakowski, TeamPassword

The biggest challenge I’ve faced as a solo founder is keeping momentum. Without energy and input from other people, it can be easy to lose faith that your product is worthwhile, and start to fall behind. The best way of overcoming this that I’ve found so far is to try and build a small network of friends you trust to share your goals and bounce ideas around with.

If you’re working alone, you need support from people who understand the exact challenges you are facing more than ever.

James Adam, Harmonia

The biggest challenge that we’ve faced over the past two years has been managing growth without wasting resources. It’s a catch-22 to having too much work to handle as a small team, adding teammates, then having to maintain a steady stream of work to pay new teammates.

We’re working on overcoming this challenge by promoting more recurring work, as well as working on a referral system to get more qualified leads through existing clients.

David Laietta, Orange Blossom Media

Growing fast without any sales or marketing staff and a tiny sales and marketing budget.

We decided to use networking principles via the web, rather than conventional techniques such as telesales and SEO.

Networking allows you to build influence and reach fast and to leverage the brand/persuasive value of established players and influencers.

Result = market leadership in 30 months.

Joe Reevy, LegalRSS

Building an audience is always a challenge. In the past I’ve built products in secret, and wondered why I could only hear crickets chirping at the public launch. But for Harpoon we decided to build our audience even before building the product. By consistently blogging, attending meetups, maintaining an email newsletter, etc., we had thousands of signups before our beta even launched.

It might be fun to work behind closed doors on a secret idea you think will change the world, but I’m convinced reaching out and building an audience from the very start is the way to go.

Andy Johnson, Harpoon

The inherent problem in locally producing goods for a small start-up company like mine is the high cost of labour. I had the idea, I had the designs, and I had to choose from two options: outsource to take advantage of cheaper labour thereby boosting my margin and perhaps suffer a little quality control or insource for ecological and quality reasons.

This was the biggest decision I made leading up to where I am at now with my company. I chose the later and am thankful every day for it. I may not have the best profit margin but I have honored my values and feel I have a very solid product that through economies of scale will one day (soon) have a great margin in addition to a great eco & sociological impact from the waste saved and the additional money I’ve injected into our local manufacturing industry.

The lesson: Think longevity and about your company’s core values and make decisions based on those, you can always work on improving the margin down the road.

Sandon Monnastes, Cup Cuff

Finding staff that are up to par with my expectations.

Matthew Baylor, Natural Selection

I had to completely shift gears and pivot (an overused word these days) the company toward the enterprise marketplace. Morphing a concierge career mentorship company such as VocationVacations to an online consumer company such as PivotPlanet was one thing; but taking the giant leap into private labeling our SaaS platform for enterprise corporate, university and large nonprofit clients was quite another.

We’re now embarking upon the exciting but scary stage of branding our new product. The placeholder name is Pivot Enterprise — but that won’t be its name for long.

After a decade of being an entrepreneur, making a 180-degree strategic business change is not to be taken lightly. It’s not for the faint of heart. However, staying flexible and resilient are essential core characteristics of any successful entrepreneur.

Brian Kurth, Pivot Planet

The biggest challenge I faced was to learn how to relax, rest and be less stressed. Sadly many of us are taught that if we work extra hard all day long we will get bigger and better results faster.
Sadly following that advice over time will cause burn out, grumpiness, loss of energy and lost ambition.

Fortunately there is a lot of research on the benefits of rest and sleep. It seems that when we step away from our work and rest is when we get the best ideas and inspirations.

What I began to do was take more breaks throughout my workday. Stepping away for a walk or simply to glance out the window to stretch and rest my eyes. I also leave some work undone at the end of the day, this allows me to feel less stress to get everything done in one day and then have something to look forward to for the next workday.

For a good nights sleep what I do is turn off all media devices two hours before I want to sleep. Then I read a good positive or inspiring book in bed before it is time to sleep. With a good nights sleep I wake up on my own with no alarm clock, full of ideas and ready to rock the day.

To reduce stress I double up the amount of time I estimate a project will take for a deadline delivery date. So, if I believe I project will take me 3 days I quote for 3 days and I set the deadline for 6 days. This way if something goes wrong I have plenty of time to fix it. However when all goes well my clients are delighted to receive the project early, which is always a nice surprise for them.

I hope this helps. It was not easy and took me many months to reprogram myself but the payoff has been huge! 🙂

Deyson Ortiz, Deyson Ortiz

The opportunities in our market are endless, so our biggest challenge is focus. We have to make sure we are only solving our customers’ most acute problem and not getting distracted elsewhere. We solve this challenge by remaining in constant communication with our target audience and doing everything within our power to allow them to speak freely.

Jeremy Bodenhamer, ShipHawk

In starting a new, state-wide network for bloggers, the hardest part for us is realizing that any new venture requires startup funds. We went on a journey where we realized we had to trust ourselves enough to have confidence in our idea and put our money where our (brilliant) ideas are. We are worth investing in.

NC Blogger Network, North Carolina Blogger Network

Most new employees want to get paid for their time and effort, and not for the result. Getting sales, marketing, PR and developers to work in a result-based environment is challenging but so much attractive for high performing individuals. Think about it – the only employees who benefit from hourly rates instead of result-based pay are below-average individuals.

Jasper Juhl, TeXovation

The biggest challenge I’ve faced is prioritization. For any startup, there’s so many different features you can build, and so many ways you can spend your time, money, and effort. But with so many possible paths to go down and such a severely limited amount of resources (you are a startup after all), prioritizing your activities can seem next-to-impossible.

The best way to overcome this difficulty is to have a clear and easily communicated vision for the future of the company. At HouseIt, we aspire to be the best possible way for people to make their dream home a reality, from start to finish.

Looking at our decisions through this lens, it becomes easier to prioritize our activities. If a task or feature gets us closer to that vision, it’s worth greater priority. If it doesn’t directly contribute to achieving our vision, chances are it can wait.

While this may be an overly simple heuristic, clearly defining a vision and communicating it to your team can ensure you keep moving in the right direction.

Griffin Thomson, HouseIt

In the opening weeks of our public beta, we recieved some positive press and hype and unexpectedly took on A LOT more users than we initially planned for. The shear volume put a large amount of stress on our product and business development campaign. The next day we could have easily built a new back end system to accommodate the critical mass, but we didn’t abandon the goals we set for that beta.

Doing so would have cost us significant time and money, and we would have lost out on an incredible amount of learning. Instead, we tweaked our beta plan to maximize what we could learn from our new (gigantic) subscriber base.

Michael Hoy, MusicBox

There isn’t a single biggest challenge. There’s always a new one every single day. With an infinite number of things to do, figuring out what you are supposed to do and when is the biggest challenge, in my opinion.

Having a routine and systems in place help you overcome these challenges. Without routines and systems, it’s difficult to prioritize items, stay productive, and have a default set of options to fallback to. Over time, hopefully the systems become more efficient and the routines more natural, and the next thing you know when the next big challenge comes you’re well trained to handle it.

Martin, Rentything

The biggest challenge for any business always involves people – attracting and keeping the right talent, and attracting and keeping customers. The secret to both is having an authentic True North. A mission that attracts, motivates, and inspires…and is real.

At Traba, we exist to help the world reach its potential, and we’re starting by empowering people to find jobs they will love. Meet anyone on our team, and you’ll see that we live by this everyday.

If you want to overcome “”the people challenge,”” then have a mission you believe in, be true to it, be disciplined in your execution of it, and the rest will take care of itself.

Terrence Cummings, Traba

The hardest part has been (and still is) to build a team with the best. Attracting the right people and being able to offer them an attractive package is always a challenge, moreover for a (mostly) bootstrapping start-up.

An interesting take away from the past few months is that compensation is not a very good predicting indicator for future performance. Lately, I have been very surprised that usually my most well compensated hires have performed the worst. My solution is as always iteration. Don’t be afraid to let go!

Sara Maria Spiller, manetch

Touriocity is a marketplace and so, as the middleman, we have to manage relationships with the customers as well as the providers. The biggest challenge we faced was keeping the tour providers engaged and happy while we continued to make fundamental changes to how the website functioned.

Rather than testing our initial providers’ patience to the limit, we decided to provide a free concierge service in which we handled all customer communication on behalf of the tour providers.

This ‘smoke and mirrors’ attitude meant that we fully understood how our platform functioned. We were acutely aware of the problems with the website on the tour provider side and so we could quickly and effectively improve the user experience before handing over full communication to the providers.

Alex Grant, Touriocity Rome

I come from an engineering background, so I like to make things. I learned Ruby on Rails thinking once I knew how to build web apps, I could launch a successful software business.

It wasn’t until I launched to crickets that I realized building the app is only half the work; I also had to learn how to market and sell it.

I’m getting better at all of it, but a key lesson for me has been that Marketing and Sales is just as important as Ruby on Rails. Now I’m slowly finding customers, and changing TaskBook to reach those customers as I learn how to market and sell TaskBook.

Josh Doody, TaskBook

The biggest challenge for myself and my team has been getting out of the mindset that building our business would be something that would earn quick results. As anyone in the startup world will tell you, building a software with real value takes time, energy, and a whole lot of caffeine.

Our team went through an accelerator, Boost VC, and were surrounded by teams that had been together for much, much longer than us. We were young. We had a basic version of our software that no one had tried out yet. We had much to learn.

Months later we have finally started to grow and I give credit to my team for separating our path from the other startups that surrounded us. We had to work in solitude for months before someone would give our software a try. We listened, we learned, we failed. In the end, we got better because we worked hard and continued to strive for building a software that could have real value. It wasn’t easy, but it’s starting to pay off.

Matt McGunagle, StrengthPortal

The biggest challenge in growing our business was having a sustainable growth, which isn’t dependent on just 1 or 2 marketing channels, but at least more than 3. Not having enough different ways and strategies to acquire new customers was something that we had to radically change and work on constantly and it was a pain at the beginning because of lots of creativity, trial and repetition that it requires.

The solution was that me and my co-founder trained ourselves to become growth hacking ninjas, and we are constantly trying new ways that would show potential in growing our user base.

Aljaz Fajmut, RankTrackr

The biggest challenge is always defining the exact area you should focus all of your efforts right now.

There will always be one defining problem which is stopping you from moving your business forward. Don’t let anything else distract you from defining that problem and solving it in the most intelligent way you can.

Hire, out-source and use software to fight the little problems that use up your time.

Read books by clever people (such as all Seth Godin books) to define your biggest problems.

Make this the last blog post you read for the next 6 months and spend your time solving the problem.

Luke Kennedy, KUDU

We grew so fast that I lost focus on managing people. Relationships died with my employees because of my zealous attention to clients.

To over come, I first set expectations clearer with new employees, then hired someone specifically to handle the internal relationships and politics so that I didn’t have to.

What I found is that 80% of business is the same as every other business, 15% is your niche and the last 5% is what makes you special. That 80% you can hire for, the 5% you can’t, so I’m focusing on that.

Domenic Venneri, Social Board

For me, the biggest challenge has undeniably been dedicating the necessary time and effort to sales and marketing. Our default behaviour as human beings is often that we focus on the things we’re good at (in my case, writing software), and we easily neglect things that we are either less skilled at, or less comfortable with.

If you’re going to start a business, don’t bother unless you know you’ll dedicate the time to sales and marketing. Several businesses later, I’ve learned, along with others, that sales and marketing matter almost more than anything else. How to overcome? Well — that’s the great question, isn’t it?

Daniel Wintschel, Recipe Cost Calculator

The biggest challenge in growing our business has been “”time.”” There are so many things that need to be done and even more things that could be done that finding the time to do everything is impossible. When time becomes a roadblock, what is inevitably the “”solution”” is prioritization.

On one side of the coin is making sure you track every possible thing you could work on. To do this, we use a combination of Slack, Asana and Zendesk. Each one. Each one is essential and helps us stay on top of everything.

Tracking aside, the real trick to prioritization is being able to decide how to order things one after the other. Because running a business has many facets, and no one is an expert in everything, we require that everyone participate in the frequent evaluation of what to do next. It helps to have a very open and conversational culture, one in which anyone can speak their mind.

Admittedly, we haven’t figured out how to manufacture time, but we have gotten pretty good at getting most out of what little time we have.

Ryan Jackson, Theorem

The biggest challenge was to make the product known and understood by the target niche. For a very specific product like PJForex this has been complex, I’ve solved this partially by starting a blog on the website, presenting a fresh view of the forex markets, and on the other side improving marketing strategies, and seeking help from a business developer.

Giulio Giraldi, PJForex

Where you’ve grown big enough that you can no longer do it all yourself, but you’re not quite big enough to justify the wages of an employee to do things for you — this is particularly true of non-billable things like answering emails.

Email takes up at least 1/3 of my day right now but it’s not really billable (most of it anyway) so to hire someone to manage it for me is just a straight uncompensated expense. Plus, most of them are things that only I know the answers to so for this to really work, I’d need a project manager (a very large growth leap).

Barbara Schendel, Wizzy Wig Web Design

The biggest challenge I have faced is the broad range of skills needed when you are the only person working on the business and so you have to do everything. I have overcome this challenge by asking for help from friends and family – if you ask everyone one simple question you can gain a lot of knowledge very easily!

Ali Gillum, MyCAW Designs

The biggest challenge so far has been designing programs for consumers who there is very little research for. Its a new field of service and as one of the first organizations applying this technique it was difficult to not have other organizations to compare success with.

As an organization that values research and analysis we were able to design a hybrid program that uses various best practices that have been proven successful in the field while implementing new techniques that we can use to collect data for future organizations that desire to do work in this area. We like to think we are trailblazing in the field of services for survivors.

Elena Bondar, Two Wings

Thinking through a go to market strategy is one of the most overlooked components of launching your startup. Creating a great product is pre-requisite. Getting people to find your solution and adopt it is at the core of what it takes to be successful in the early stage. For most startups, acquiring users through paid acquisition is cost prohibitive. So you have to be really creative to get the most out of free acquisition channels.

To overcome the challenge, it’s often helpful to start small. Find a core problem for a subset of the market and then gradually expand your vision. Building into other platforms is a great way to acquire users without having to pay a fortune on customer acquisition. In doing so you can really differentiate your software as well from existing solutions.

Daniel Tawfik, Vonjour

Hands down, my biggest challenge was wanting things to be perfect. While building the business, I wanted to build it right so that we wouldn’t have technical or administrative debt down the line.

In hindsight, quick is almost always better than perfect. In a growing business, something delivered tomorrow at 80% ok is waaaay better than something delivered next week at 99% ok.

We’ve transitioned to focusing the extra energy on our customers, and boy it’s paid off in spades. Our team is happier, our clients are happier, and we’re still growing.

Toufan Rahimpour, LogoWorks

So far the biggest challenge I have faced is balancing my time between my family, my day job, and Alabaster. Thankfully, I have a supportive wife and daughter. Every Wednesday and Saturday, I get to work undisturbed on Alabaster products and projects, and often during the week, I will get a couple of extra hours.

Jake White, Alabaster

The biggest and most defining challenge I faced with growing MonthlyStash was letting go of the fear of rejection.

In the early days, I was developing the platform, acquiring products and brainstorming my next steps on my own. In short time, I hit a wall and accepted I couldn’t turn MonthlyStash into a business by myself.

I needed help, but asking for it didn’t come easy. I was afraid my peers wouldn’t believe in me or in my idea. I was afraid of being rejected if my idea wasn’t “good enough”.

I overcame this fear by looking into the mirror and asking myself to honestly answer the question, “”do I believe in this?””. If you don’t believe then it will never be. If you believe, and are passionate then people will line up to help you. And that’s exactly what happened. I identified my weaknesses and pitched the opportunities to my peers.

A short time later, I am no longer facing the challenges alone! We’re a small, but intelligent and united team. I wouldn’t be here today, growing MonthlyStash if I succumbed to the fear of rejection and never asked for help.

Hunter Meyer, MonthlyStash

My biggest challenge would have to be keeping a proper balance in the Sell/Make cycle. You have to sell something to pay the rent, but you have to make it quickly enough to go out and sell the next thing. It’s very easy to lose track of that and quickly get in over your head.

That and working with other people sometimes. Be wary of who you partner with. They can be the helping hand you need or the noose around your neck.

Stephen Walcher, Stephen Walcher

My cofounder and I both have families with young kids. We are always resource constrained. We find ourselves saying “if only we had ___” a lot. It can get discouraging. But, we also have families to feed.. which keeps us moving forward at all times. Not nearly as fast as we like… but we are playing the long game. We hear the quiet whispers of “why don’t you just get a job?” quite a bit… but, we know that that is not who we are. We are warriors. We are entrepreneurs.

Geoffrey Baron, HelpYouSponsor (HYS)

The biggest challenge for any start-up entrepreneur is to find a calm and consistent focus amongst the many ups and downs. One minute you’re experiencing great euphoria as you make your first sale and then the next minute you’re in deep despair because you only made one sale.

Start-ups take time. Progress takes time. Dealing with and enjoying these ups and downs is a big part of running a start up. Learn to deal with them and you’ll keep a clear head ready to deal with the many other challenges you’ll face.

Henry Walton, PrizeAid

I think one of the challenges that many startups face is getting the word out. Our team is engineering-centric, which means we’re able to build an awesome product quickly, but we’re not always as good at the ‘softer’ side of things.

We’ve tried to meet in the middle with our marketing efforts, applying an engineering and analytical mindset to how we reach people. Doing that may not work as well for a huge mega-brand, but for a startup it really lets us focus on what works… and we still get to be engineers while doing it!

P.S. We’re also on the hunt for an ‘analytical marketer’ right now: somebody that can bridge the gap between the business side and hardcore analytics. If that’s you, we’d love to talk!

David Ordal, EverBooked

The hardest thing is building the team. Everyday you have to fight to hire talented people and keep the people you’ve already hired, motivated.

David Okuniev, Typeform

The founders are 3 creatives so the the biggest challenge was finding the technical right team to build what is a very sophisticated personalisation platform. To overcome this challenge we had to immerse ourselves in the technical side of things and decipher the technical talk and finally find the right people with the right personality and skills to do the job. It’s a steep learning curve but we’re getting there.

Jonny, The Book of Everyone

As a non-technical co-founder, one of the biggest challenges is finding technical talent and eventually a CTO. You don’t just want someone with technical ability, you want a person who buys into the vision, understands the business, and can grow to manage others.

Believe it or not, that person is probably somewhere in your network, you just have to dig deep. Put out feelers to every groups of friends, family, former co-workers etc., that you can think of and you’ll be surprised what you find. Our CTO is a friend of a friend from college.

Grant, Curbside Care

Confidence. It’s very easy to fall victim to Imposter Syndrome, especially when you’re striking out on your own. Do I know enough to justify asking people to pay me? Am I really an expert?

Reaching out to other people in my network helped me realize that a) pretty much everyone feels this way, even the ‘successful’ people and b) you don’t have to know everything to be an expert to the clients you serve – you just need to know more than they do (and, of course, enough to be able to solve their challenges). Once my confidence improved, my business started to take off.

Tracy Bradley, webbedUP

People. Finding the right leadership team – and then convincing them this is the right “next opportunity”! and then of course every last appointment under that team. We start with ownership – everyone at ShippingEasy has options in the business.

Then, we set goals and invest the time to communicate progress against them continuously. Transparency is probably the word I would choose for overcoming the people challenge. We just don’t have turnover – our team feels ownership and they stay.

Katie May, ShippingEasy

Finding product-market fit.

We’ve built a team that can iterate through ideas very quickly. Our business teammates come up w/ ideas, and then our technical teammates build them out. We’ve been able to get down to weekly iterations, which has accelerated our ability to move towards product/market fit.

Aki, MarketMuse

My biggest challenge is to not be so hard on myself. I’m constantly second guessing decisions, directions and focus. Lately I’ve taken a step back from the keyboard and refocused.

One small thing that has helped me in a big way was not using pseudonyms online. It’s been the norm for me to stay anonymous because it’s a safety shield. If I said something stupid, it didn’t matter, nobody knew who I was. When I removed the “mask” it felt a little weird for a short time, but I got over it quickly. Now, whatever I say reflects on me and my business. This creates accountability and motivation.

Paul Dessert, Resume Beacon

The biggest challenge we currently face is knowing when and how to make the appropriate market pivot. New customer populations are emerging (good problem to have) that have us asking – who truly is our target population?

Not willing to miss any opportunity, we are reconfiguring how our product is delivered. This has required us to listen to the customer, accommodating needs regarding product delivery, purchasing, and interactivity. With that said, we have not abandoned our original customer base or business model but are allowing our model to evolve as changes, customers, and needs arise.

Matt Bratcher, Simulus Learning

When I decided to start my business I had no savings and was three months into my marriage. Quitting my job was not an option, so I found myself working full time in addition to running my own business. A lack of time was my biggest obstacle, and with it came a struggle to know how to use my limited time.

I learned to prioritize tasks in this order: 1. Work that gives us enough to live for a few more weeks. (full time job, client billing hours, etc.) 2. Work that has a high likelihood of resulting in future, long term revenue, but is harder to measure (website optimization, customer service, etc.) and 3. Work that could turn into a lot of profit long term, but is entirely uncertain (new products or features).

It took 18 months before I was finally able to quit my day job, but I did it without taking out a loan, mortgaging my home, or piling on credit card debt. I wouldn’t have it any other way.

Jeremiah Prummer, WP Overnight

Biggest challenge was figuring out what users really want.

Our short story:

I had a referral recruiting product, Eventually we discovered our users wanted a way to discover new opportunities for themselves.

So we pivoted to a passive job search platform: Careerswitch.me .Its a place where you can discretely state your career aspirations and get aligning job offers while you continue working.

To figure what we should build here are few things we did:

1. Get out of the building – I would walk into a cafe and interview people about their job search experience. Then I would show our prototype and get feedback. Linkedin/Facebook was costing me $50 to acquire an unknown customer. In cafe, I would buy people coffee, chat to understand their personal requirements and then make them our users. Win!

2. Help your customers even before you have the product – Soon, my friends saw me as thought leader in recruiting. They would email or call me when looking for a career switch. I would advise them, have them referred to employers, make introductions etc.Sincerely helping your early adapters helps to create your product champions. Now these people refer their friends to Careerswitch.me.

Here are few things I understood through customer interviews:

1. Don’t ask users about solutions. Empathize with their problems and iterate on multiple solution yourself.

2. Don’t start with your best grand idea but a much smaller version of your idea that would get adaption.

To quote Dave Mclure “”Customers don’t care about your solution, they care about their problems”

Pavan, CareerSwitch

The biggest challenge has been dealing with all of the conflicting advice you get. Every person you sit down with will give you a different direction that worked for them. This is quickly overwhelming and incredibly distracting. What we have learned to do is to just keep telling our story, why we started, and how we want to impact the world. When we ask for advice now, we stick to people who can help us accomplish that.

Caleb LeNoir, Liquid

Biggest challenge in growing our business is to go from an idea to a real service. This takes great amount of planning and networking which makes tools like Skype, Gdocs and calendar applications essential

Raoul, Veduo

In an early stage startup you end up trying anything and everything to get traction. Most of it is just not going to work, and you won’t know what works until you try. The biggest challenge is trying again.

To grow a company you need to recognize that failure is going to be your breakfast, lunch, and dinner. Embrace it. Love it. And don’t take it personally.

Keegan Dwyer, shortcutFoo

One of the biggest challenges we have faced is getting our product in front of our target demographic, and we are constantly working towards this goal. We have learned the importance of being selective on what press we choose to interact with. It’s always great to get a write up, but you want to be attracting your target customers, not just fair weather fans.

Katie Crooks-Branch, PIGMENT + PALETTE

When the company grows, it is very easy to get distracted on things which are not so important. We are trying to outsource all monotonous tasks that are needed to be done and to just forget about non-crucial stuff.

Alex Kravets, Topic

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Written by Smash.vc

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