Common Challenges Faced by New Firm Owners

I’ve coached 50+ founders. These are the 4 topics that get 95% of our time (especially #3): 1️⃣ People Problems There is a joy of being connected with people, and sometimes a friction. And there are all sorts of relationships to manage: cofounders, board members, investors, employees, customers, family, friends…so some frictions are guaranteed. When people problems surface, the temptation is believe the issue is in them. But the common denominator in every relationship is yourself. Anytime we’re working people stuff, we always start with you. First, identifying underlying needs. Then getting better at both giving feedback and managing to meet everyone’s needs. People problems require brave conversations. So we clarify what needs to be said, what needs to be heard, and then we commit to actually having the conversation. 2️⃣ Breaking Down Silos Most growing teams develop strong functional areas that begin to operate as their own micro businesses, rather than a collective system. When company leadership isn’t performing as one unit, politics and localized thinking take root. Decision making gets bogged down. Performance drops off. Silos crumble by establishing a ‘first team’ culture within the leadership team. We identify ways to build trust, foster candor, and develop collective commitment. We role play the hard conversations that it takes to drive this level of culture change. 3️⃣ The Inner Game Building a company is relentless. New challenges surface weekly, if not daily. The company can begin to feel like a hungry beast that can never be fed enough energy or attention. And burnout looms as a possibility if not already a reality. For others, impostor syndrome and self-doubt become persistent stumbling blocks. The inner game of leadership challenges everyone. We just don't want to admit it. At times, I’m a sounding board. Other times I bring compassion. And others, I challenge the beliefs that no longer serve them. This is deep work. For many, it’s the highest leverage work to be done: clearing out the mindsets that got you here but won’t get you there. 4️⃣ High Stakes Decisions One of the hardest parts of being a founder is that as the company grows there are fewer and fewer people who you feel comfortable being real with. Doubts about big decisions become solitary exercises of swirling thinking. Some questions are strategic: - Do we need to pivot? - Should I hire a COO now? Some are existential: - Should we look for an acquirer or keep building? - Do I even want to be the CEO? When big decisions surface, we slow down. We take time to listen to the parts of ourselves advocating for different decisions. We explore. Sometimes things need to move fast, other times they need to simmer. And then we take the right action for the current moment. — Hoping that by sharing, you feel a bit less alone in the journey. This stuff isn’t easy. If a conversation about any of the above might help, reach out.

🛑 The Unspoken Reality: Navigating the 5 'D's in Business 🛑 Yes I am going there! Challenges are as certain as change itself in the life of every business. Yet, many leaders often overlook planning for the critical yet unforeseen. Let's discuss the 5 Ds—death, Disability, Divorce, Disagreement, and Distress—and their profound impact on businesses, often leaving them in turmoil and an unprepared family trying to pick up the pieces. 1. Death 💔: It's uncomfortable yet necessary to confront. The passing of a key figure can destabilize operations and leadership. The National Association of Corporate Directors found that less than 25% of private companies have a formal succession plan in place. What’s more, does the family know the plan, and who is the successor to represent the estate’s interest in the business? 2. Disability 🚑: Unexpected health issues can sideline crucial contributors, disrupting business flow. The Council for Disability Awareness notes that 1 in 4 of today's 20-year-olds will become disabled before retirement. 3. Divorce 💔: Personal life events can spill over into the business, affecting ownership, operations, and morale. The American Academy of Matrimonial Lawyers study found that businesses are involved in 62% of divorces. 4. Disagreement 🤝: Cohesion is key. When partners or leaders disagree fundamentally, it can cripple a business. I’ve seen it first hand inside clients. Harvard Business Review highlights that 65% of startups fail due to co-founder conflict.   5. Distress 😰: Economic downturns, market shifts, or sudden loss of business can lead to critical stress points. Bloomberg states that 20% of small businesses fail in their first year, a number often exacerbated by inadequate planning for distress. Each of these 'D's poses a significant risk, yet, with foresight and strategy, their impact can be mitigated. Harvard Business Review found that over 70% of businesses don’t have a solid plan for these scenarios. That’s a staggering number! 📉 🔍 Many first-generation business owners have a high-risk profile to get the business required, and as they grow, they ignore what could destroy their life’s work in short order. Risk management is not merely an option; it's a necessity. Cultivating resilience against these 5 'D's involves: Establishing a robust succession and estate plan. Insuring against disability and operational disruptions. Preparing a prenuptial or buy-sell agreement in partnership scenarios. Encouraging open, constructive dialogue among leaders. Maintaining a healthy emergency fund and diversifying income streams. It's about transforming potential vulnerabilities into strengths, ensuring your business survives and thrives, irrespective of its challenges. 👥 Have you identified any of the 5 'D's as potential risks within your own business? What steps have you taken to safeguard your enterprise against them? Let's discuss below 👇.

🚀 From Challenges to Triumphs: Stumbling Blocks for Founders and How to Avoid Them. As someone deeply immersed in the SF Bay Area startup scene, I’ve worked with hundreds of founders, helping them refine pitches, hone marketing strategies, and develop GTM plans. The founder’s journey is rewarding but full of challenges. Here are some common obstacles and strategies to overcome them: 1. Navigating Uncertainty Market conditions and customer preferences change rapidly. Strategy: Embrace flexibility. Gather feedback, iterate, and be willing to pivot. 2. Securing Funding Raising capital can be daunting. Strategy: Develop a strong fundraising strategy. Create a compelling pitch deck, practice your pitch, and build a network of investors. **Get your data room in order**. Rejection is part of the process—use feedback to improve. 3. Building the Right Team Finding individuals who share your vision can be challenging. Strategy: Create a strong culture and clearly communicate your vision. Sometimes, the right contractors as fractional assistance are priceless. 4. Managing Time and Resources Founders often juggle many responsibilities. Strategy: Prioritize tasks, delegate, and use AI to reduce time on repetitive tasks. Take care of your well-being to sustain productivity. 5. Scaling Operations Maintaining quality and efficiency during growth is challenging. Strategy: Develop scalable processes and systems. Continuously evaluate and optimize operations. 6. Balancing Vision with Feedback Balancing your product vision with customer feedback is essential. Strategy: Stay true to your vision but remain open to feedback. Use insights to improve your product. 7. Overcoming Self-Doubt Imposter syndrome can affect even the most confident founders. Strategy: Build a support network. Remember, 80% is mindset—work on it daily. Celebrate small wins to boost confidence. Final Thoughts: Being a founder is challenging, but with the right strategies and mindset, you can succeed. Every obstacle is an opportunity to learn and grow. Stay resilient, keep pushing forward, and never lose sight of your vision. Having worked with hundreds of founders in the SF Bay Area, I’ve seen how dedication and the right strategies turn challenges into success. Are you a founder facing these challenges? Share your experiences and strategies in the comments below! Help support founders on this journey. 💪✨ #StartupLife #Founders #Entrepreneurship #OvercomingChallenges #StartupSuccess #Leadership #Innovation #SFBayArea --- This title aims to capture attention and encourage readers to learn more about overcoming common startup challenges.

After 300+ coaching calls with high-performing founders… I’ve realized that even the best go through the same 10 biggest struggles: — 1. Imposter syndrome 95% of founders are living with imposter syndrome: • Doubting your abilities • Fear of being "found out" as a fraud • Think your success came from luck, not years of work But here's he hack: EVERYONE else feels like an imposter too - It’s happening because the challenge level that you’re facing is bigger than your current skillset. — 2. Lack of confidence Lack of confidence = Lack of evidence. Usually this comes from two things: • Past trauma • Shooting too high above your current skill set A coach/mentor will help you build confidence over these huge challenges with the right support. — 3. Don’t have the resources Being a founder = A LOT of being creative with financial constraints. Flexibility is key. When resources are scarce: Re-evaluate, make suboptimal decisions and pivot. — 4. Lack of clarity I've seen high-performing founders execute amazingly when they just have clarity and confidence. No clarity: • Dread important decisions • Procrastinate • Pay huge costs Make having crystal clear clarity your priority. — 5. Want to do everything alone Why struggle on your own when you can learn from 10,000 hours of failures ahead of you. The reason why I invested 5 figures into Matt Gray's Personal Branding Mastermind for my content strategy, so that I can scale faster. It’s NOT smarter to do everything alone. — 6. Resourcefulness The internet gives you access to everything and everyone you need. Don’t know how to do X → teach yourself the skill → done Your biggest founder superpower is resourcefulness. — 7. Vulnerability Founders are at war with: • Competitors • Suppliers • Clients It’s very, VERY hard to have a space to be vulnerable about all that. You have to force yourself to clear the sh*t out and RESET. — 8. Old software (limiting beliefs) getting in the way of achieving. Like a coach and a player: You can’t take action on the field and observe yourself at the same time. Nobody can see their own blind spots. — 9. The biggest bottleneck is YOU Founders put all the weight on their shoulders. → They see their employees counting on them. → They think they need to do all the things no one else can do. Don’t let your fear of delegating stunt your company’s growth. — 10. Extreme loneliness Many years in my entrepreneur career I’ve felt extreme loneliess (Especially when facing crucial decisions as CEO of a 100-person company) I wanted to “save” money. But I suffered the consequences. It wasn’t until I co-founded the EO Argentina in 2013 that I realized I didn’t have to go through these struggles alone. And neither do you. No matter what you’re going through. People have been through your situation 1000x before. You do NOT have to go through this alone. Reach out today!

98% of startups fail within the first 5 years! . . . Here's the thing - most of these failures aren't random. They're battle scars from common mistakes. So, let's dissect a few of the biggest culprits: 1. Lack of Product Market Fit: You should solve a real problem people actually care about. This means research, customer discovery, and being willing to pivot if your initial idea flops. Don't be afraid to iterate - sometimes the best ideas are born from the ashes of failed attempts. 2. Reaching for the Stars (Too Soon): Everyone dreams of building the next Google. Scaling too fast is a recipe for disaster. Focus on building a solid foundation first. That means nailing your core offering, understanding your unit economics, and learning to walk before you try to fly. 3. The Business Model Black Hole: This one's a silent killer. Without a clear roadmap to profitability, you're toast. Invest time in understanding your target market, pricing strategy, and sales channels. Think of your business model as the engine that drives your growth - you should make sure it's running smoothly. 4. Marketing: Building a great product is only half the battle. If nobody knows you exist, it's all for nothing. Don't neglect marketing and sales! Content marketing, social media, targeted campaigns - these are your weapons to cut through the noise and reach your ideal customer. 5. Adaptability? What Adaptability? The market is a living, breathing beast. It's constantly evolving, and you should move with it. Stay on top of trends, be willing to pivot when needed, and embrace an agile mindset. Remember, the most successful startups are the ones that can learn, adapt, and conquer. What are your biggest startup struggles?

What’s really keeping business owners stuck? I asked—and here’s what they told me. I had calls with 7 business owners recently— from tech, consulting, coaching, and creative industries I had conversations that went deeper— beneath the strategy, the schedule, and the software Have you ever… • Felt pulled in every direction? • Questioned what to do next? • Wondered if you’re the only one struggling? They told me the truth And it wasn’t a lack of tools It was burnout. Confusion. Isolation One founder told me: "I started this for freedom. Now I feel trapped." That hit hard Because I’ve felt it too When I saw the same themes show up again and again, I knew I had to share them And they're not alone—and the data proves it. Every single pain point here is backed by real statistics from studies on small business owners and entrepreneurs ⚠️ 8 PAIN POINTS KEEPING BUSINESS OWNERS STUCK ❌ Burnout → Stretched too thin → Trying to do everything alone → Started for freedom, got overwhelm instead → 42% of small business owners experienced burnout last month → https://lnkd.in/edi4QPvE ❌ Clarity → Too many ideas → No clear direction → Stuck overthinking → 27% say “knowing what to do next” is a top need in marketing → https://lnkd.in/eqM2h8kj ❌ Chaos → Don’t know what to delegate or automate → Tech and tools not in place → Lacking systems or processes → 70% spend 45 minutes to 3 hours daily on tasks that could be automated → https://lnkd.in/eK6Qewwt ❌ Connections → Can’t reach the right people → No warm intros → Great offer, no access → 49% cite lack of networks/mentors as a major growth barrier → https://lnkd.in/ex3f-rPU ❌ Isolation → Building it alone → No one to talk to → Tired of figuring it out solo → 26.9% of entrepreneurs feel lonely or isolated → https://lnkd.in/ebKH2rAV ❌ Money → Sales not coming in → Working nonstop with little return → No breathing room → 39.2% of entrepreneurs have financial worries → https://lnkd.in/eetHUgay ❌ Marketing → Can’t explain what they offer → No consistent way to attract leads → Content isn’t converting → 73% aren’t confident their marketing drives business goals → https://lnkd.in/eAQDNSMT ❌ Mentorship → Don’t want another course → Need real feedback → Want someone who gets it → 70% want help with marketing strategy but lack time/knowledge → https://lnkd.in/eYJe-pgr Struggles are a sign you’re building something that matters. Want to rewrite your entrepreneur story—with clarity and confidence? Book a free clarity call—link in Featured Section ♻ Repost if this list hit home for you or someone you know 👋🏻 Follow Stephanie Hills, Ph.D. to build a business and life you love