What is the most unexpected challenge you’ve faced as a founder?
Morgane Granier
46 replies
Being a founder comes with countless challenges, but some of the toughest ones are often the least expected.
Let’s share stories about those surprising obstacles that caught us off guard—whether it’s a team issue, market change, or something totally unexpected.
Replies
Alexander Galitsky@ag94
That you have to actually talk to your customers 😭
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Launching soon!
@ag94 hahahaha YES! Saas founders usually think they won't have to 'cause they want it to be selfserve services, but spoiler alert... we have to! 😂 Been there too but I'm actually starting to like talking to my users
(Love your comments btw. Second punchline you're throwing under one of my discussions)
@morgane_glt hopefully soon AI will help us, socially-anxiously-awkward introverts, avoid it 🥰
Launching soon!
One of the most unexpected challenges I faced as a founder was managing my own energy and mental resilience. Balancing the constant ups and downs, staying motivated, and avoiding burnout proved to be just as critical—and difficult—as tackling any business problem 🥵
@morgane_glt You should be proactive about Scaling team culture, Managing remote teams and Maintaining work-life balance as you get closer to your launch :)
Probably managing yourself, especially in the early days where it is just you (+ co-founder(s)). Sometimes it's difficult to get going and get in the flow of getting things done. I think there is a lot of focus on how to manage teams, how to raise, growth hacking, ... while not too much on managing yourself. It's a learning curve for sure.
Launching soon!
@robin_poelmans Completely agree. There's a lot to think about and manage at the same time. Keep your vision alive, nurturing your relationship with your co-founder and ensure you're on the same page, but also get shit done product, marketing and growth-wise.
So challenging but so exciting!
@morgane_glt CEO at an early stage company = Chief Everything Officer 😂
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@robin_poelmans Hahahaha so true 😂 Love it
Self Doubt. As a first time founder
I struggled with realizing my value at first.
Learning so many new things and wearing different hats can be exhausting.
I fail every single day in one way or another.
Now, instead of feeling like an imposter I remind myself that I’m human.
There’s things I don’t know how to do, things I don’t like to do, and things I will never be the best at.
That’s okay.
My best quality is being aware of what I’m capable of and if I can’t get it done I’ll find my clients someone who will .
Launching soon!
@ashley_bergeron So relatable! Imposter syndrome can sneak up on you, but your self-awareness is such a superpower. Keep reminding yourself that progress over perfection is what really counts!
The most surprising hurdle for me was dealing with sudden market shifts that left our plans in disarray. Adapting quickly and realigning our strategy was more challenging than I initially anticipated. 📉
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@ayla_reynolds Those unexpected market changes can really throw you off course. Adapting quickly is never easy, but it’s what sets great founders apart. You’ve got this!
Sparky
For a bootstrap founder, a limited marketing budget can indeed be a big challenge.
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@liu_kexin Bootstrapping on a shoestring budget is no joke. Finding creative ways to stretch every dollar can be exhausting but also super rewarding when it pays off!
I was surprised by how difficult it may be to stay motivated during terrible times.
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@nathaniel_cross It’s so true, staying motivated when things aren’t going well is one of the hardest parts. But those tough times really do build resilience!
I didn't anticipate dealing with unanticipated regulatory difficulties. It was a serious setback.
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@amelia__waters Regulatory hiccups can feel like a sucker punch—totally get it. They’re such a wild card, but getting through them just makes you a stronger founder!
One of my biggest surprises was realizing how challenging it can be to manage unexpected team dynamics. It’s one thing to plan for market changes, but people issues can really throw you off!
Launching soon!
@elido_dial People challenges are always the sneaky ones that catch you off guard! It’s a whole different beast compared to market shifts. You’ve got this!
One of the most unexpected challenges I faced the dealing with the emotional toll of constantly pivoting. I had to learn how to manage stress and stay focused amidst the uncertainty.
Launching soon!
@sandy_leventh Constantly pivoting can really take it out of you emotionally. The mental game is real, and staying focused amid all the changes is a massive win in itself.
I was surprised by how challenging it could be to balance vision with day-to-day operations. Keeping the big picture in mind while managing daily tasks proved to be trickier than I expected.
Launching soon!
@saige_makenna Walking that tightrope between the big picture and day-to-day grind is harder than it seems! It’s like you’re wearing two completely different hats all the time.
I was caught off guard by how much time and effort goes into maintaining a positive company culture. It’s easy to focus on the product, but keeping the team motivated is a whole different challenge.
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@rose_linda Keeping the team motivated is a whole job in itself! It’s so easy to get lost in product goals, but without a strong team vibe, things can quickly go south.
Balancing work and life was tougher than I imagined. It took more effort to manage than I expected.
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@noora_mccluskey I feel you on the work-life balance struggle! It’s easy to let things blend when you’re passionate, but finding that line takes serious effort. Glad you’re tackling it!
I was surprised by how much time I spent on legal and administrative tasks. I didn’t realize how crucial it was to have a good team to handle these aspects so I could focus on growth.
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@isabella_wandrei The unglamorous side of being a founder, right? Legal and admin work can be such time-eaters. Finding the right people to handle those parts makes all the difference!
one of the most surprising issue encountered was managing team dynamics.
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@bartosz_strickland People problems are so real! You can have the best strategy, but team dynamics can make or break everything. It’s always a learning process—thanks for sharing!
An unexpected challenge was dealing with regulatory changes that impacted our product development. Keeping up with new laws and adjusting our approach was a real curveball.
Launching soon!
@emmawalsh Keeping up with regulations feels like playing a never-ending game of whack-a-mole! It’s one of those things you don’t think about until it hits you. Hats off for navigating those!
I was caught off guard by how much effort it takes to build a strong company culture remotely. Creating a cohesive and motivated team without in person interactions has been tougher than I imagined.
Launching soon!
@alicia_klein Building culture remotely is such an underrated challenge! It’s tough to recreate that in-person vibe over Zoom. You’re not alone; it’s a whole new skill set we’ve all had to learn!
I hadn't expected market changes to hit us so everly We needed to pivot swiftly in order to remain relevant.
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@ellareyes Market shifts can be brutal, right? Pivoting on the fly is no joke... Kudos for adapting!
Finding the perfect work-life balance was more difficuilt than I had anticipated. I assumed I could manage everything, but there's been a learning curve.
Launching soon!
@susie_johns Oh, I hear you! 😅 It’s one of those things that seems manageable until you’re in the thick of it. But hey, figuring it out bit by bit is part of the journey—props to you for navigating that learning curve!
For me, the most unexpected challenge was learning how to effectively delegate and let go of control. As a founder, it's tempting to want to be involved in every decision and handle everything yourself. But I quickly learned that's not sustainable and can actually hold your company back from growth. Building a strong team you can trust and empowering them to take ownership was a big mindset shift, but so critical for scaling the business and maintaining my own sanity! 🧘♂
Launching soon!
@noahchristopherbennett Letting go of control is such a big shift, but you nailed it—trusting your team and letting them take ownership is a game-changer for scaling and keeping your sanity intact!