We reached out to 68 startup entrepreneurs to ask them what they have found most challenging about starting and running their startups. Heaps of mixed views here, which makes for great reading.
“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 successfull 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 travelling from one city to an other (sort of hackaton on a train). Certainly a great marketing stunt but very expensive to get a train only for you for free…
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, Molander
“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 honoured 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
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