Gary Taylor’s Post

The founder CEO is, no question, the driving force behind a start-up—but scaling start-ups also need a team of high-performing senior leaders to achieve their growth goals (see sidebar A word about CEO succession in start-ups)

Leadership isn’t about how many points you put on the board for yourself, but how many you help others score. This is my core. In the last six months at Constellation, I’ve shifted my focus soon after joining from personal wins to lifting up the next generation of leaders. I’ve carved out time to send deals to others—up-and-comers, the next wave of talent. My approach has been simple: How can I help you? I don’t consider myself a leader in the traditional sense. I prefer leading from the center, supporting, empowering, and offering guidance wherever I can. It hasn’t been perfect. I couldn’t always deliver on every request. But I’ve always focused on quality over quantity—it’s not about how many deals you close but about the impact of each one. And I’ve led with founder empathy—understanding what founders are going through and being there to support their journey. After almost two decades in venture capital, I’ve shared what I know freely, giving others the choice to take what resonated. Wherever I am, I aim to leave things a little better than I found them. And for me, that’s what real leadership is all about. Here are two ways I’ve found to help others in M&A or venture: 1. Be a Connector, Not Just a Deal Maker: Introduce people to valuable connections, even if there’s no immediate benefit for you. Whether it’s founders seeking strategic advice or investors looking for opportunities, being a connector builds trust and long-term relationships that often lead to unexpected wins. 2. Share Knowledge and Experience Freely: Don’t hold back insights from your own journey. Sharing what you’ve learned—whether it’s about structuring deals, negotiating, or understanding market trends—empowers others to make better decisions. Even if they don’t use your advice, the generosity in sharing builds goodwill and stronger partnerships. What’s your approach to supporting others in their growth? #Leadership #Mentorship #NextGeneration #Empowerment #VentureCapital #LeadFromTheCenter #FounderEmpathy #QualityOverQuantity

Almost every CEO/Founder knows their Direct Sales and Partner Sales should be accelerating faster than the current pace but can’t figure out the root cause. Tired of missing revenue targets and key business milestones? Tap into our Fractional Executives Services and accelerate your companies success.

Is your startup struggling to find its footing? You're not alone. Many founders feel the weight of the world on their shoulders, especially when navigating the choppy waters of a startup environment. But what if I told you that the key to success lies in your leadership? This blog post unpacks 6 crucial reasons why strong business leadership is the secret sauce for startup success: - Setting a Clear Vision and Strategy: A clear vision acts as a roadmap, guiding your team and ensuring everyone is moving in the same direction. - Building and Managing a Strong Team: Recruiting and retaining top talent is essential, but it's equally important to foster a culture of open communication and collaboration. - Making Critical Decisions with Limited Resources: Learn how to weigh risks and benefits effectively, especially when resources are tight. - The Importance of Transparency and Honesty: Open communication builds trust and empowers your team to contribute their best work. - Providing Opportunities for Growth and Development: Invest in your team's development by providing training and mentorship opportunities. - Leading by Example: Inspire your team by embodying the startup's values and work ethic. Ready to become the captain your team needs? Dive into the full blog post below.

I remember when I could name every person in our office. Now, with our recent expansion, I pass faces in the hallway I don't recognize. And if I'm being honest? Sometimes it makes me feel like I'm fading into the background. Our company's growth is exciting - new offices, new markets, new opportunities. But it's also bringing up some unexpected emotions. That startup energy where everyone wore multiple hats? It's evolving into structured roles and formal processes. But here's what I'm learning: • Feeling growing pains doesn't mean you're failing • Structure isn't the enemy of innovation • Your original impact doesn't diminish with company size • Sometimes you need to redefine your role instead of waiting for someone else to do it Growth means change, and change isn't always comfortable. But maybe that's okay. Maybe feeling a bit lost is part of finding your new place in a bigger picture. #CompanyGrowth #CareerDevelopment #ProfessionalGrowth #Authenticity #Leadership

🌱 Building a startup from scratch to a developed stage involves significant leadership evolution. 🌟 🔹 Stage 1: The Inception (Level 1 Leadership) ✨ Starting from Scratch Initially, founders handle every aspect of the business. This phase is marked by resource constraints, intensive time management, and the challenge of building a brand with limited visibility. Challenges: 💸 Limited funds and resources. ⏰ Long working hours and personal sacrifices. 🎨 Establishing brand identity. Overcoming Challenges: 💪 Passion and commitment drive momentum. 📚 Continuous learning and adaptation refine strategy. 🤝 Networking aids mentorship and initial customer acquisition. 🔹 Stage 2: Growing Phase (Transition to Level 2 Leadership) 🌱 From Hands-On to Delegation As the startup grows, delegation and structured roles become essential. Founders identify and appoint key team members to handle specific responsibilities. Challenges: 👥 Finding the right talent. 🔑 Trusting others with critical tasks. 🌐 Maintaining company culture. Overcoming Challenges: 🎯 Strategic hiring aligns with the company’s vision. 🗣️ Clear communication establishes expectations. 🌟 Empowering team members fosters ownership and accountability. 🔹 Stage 3: Developed Stage (Multiple Levels of Leadership) 📈 Structured Leadership and Scalability In the developed stage, multiple leadership levels are established, with founders focusing on long-term strategy. Challenges: 🚀 Developing leadership skills at various levels. 🛠️ Ensuring consistency in operations and values. ⚖️ Balancing daily operations with strategic planning. Overcoming Challenges: 🎓 Implementing leadership development programs. 📋 Establishing robust processes for consistency. 📢 Regularly communicating the company’s vision for alignment. 🏆 At Monkey Ads & Studios, we have successfully transitioned to the developed stage with multiple levels of leadership. Our focus has shifted to long-term strategic planning, allowing us to invest heavily in research and development as well as continuous training. By doing so, we ensure that our team is well-prepared to tackle future challenges and innovate within the ever-evolving digital marketing landscape. This commitment to growth and excellence empowers our leaders at all levels to drive our vision forward, maintaining the consistency and values that define our brand. 🌟 #Leadership #StartupJourney #Entrepreneurship #BusinessGrowth #StrategicPlanning #Innovation #DigitalMarketing #MonkeyAdsAndStudios #LeadershipDevelopment #WomenInBusiness #GrowthMindset 

Founder Mode Hack: Use Fractional Execs! As a founder, staying deeply connected to the core functions of your business is critical. Paul Graham’s concept of “Founder Mode” highlights the unique state of focus and immersion that allows founders to drive their companies forward with unparalleled energy and insight. But as your business scales, how do you maintain this laser focus without getting bogged down by the operational complexities of growth? Enter fractional leaders. Fractional executives—CROs, CMOs, CTOs—are seasoned professionals who provide expert leadership on a part-time basis, without the long-term commitment or equity stake that full-time hires often require. Here’s why they are a smart tool for founders looking to grow faster while staying close to their business: 1. Preserve Your ‘Founder Mode’: Fractional leaders handle critical projects or functions, allowing you to remain in the strategic ‘Founder Mode’ that Paul Graham talks about. They take on the heavy lifting in areas that may not be your strength, freeing you to focus on what you do best—vision, product, and customer experience. 2. Cost-Effective Expertise: Unlike full-time executives who require significant compensation packages and equity, fractionals work on a project basis, often costing a fraction of a permanent hire. Their goal is to execute, deliver results, and then step back, all without diluting your ownership. 3. Agility in Execution: Fractional leaders are not there to entrench themselves in your company. Their purpose is to quickly assess, act, and hand off to your internal team. Their work is documented in a clear SOW (Statement of Work), with measurable outcomes that allow you to see the impact compared to the prior state. 4. No Strings Attached: Because fractionals aren’t seeking equity or long-term roles, they bring an unbiased, results-driven mindset to your business. They are focused on getting the job done efficiently and effectively, with a clear exit strategy in place from day one. In short, fractional leaders enable founders to stay in the driver’s seat of their business, ensuring that growth doesn’t come at the expense of strategic focus. They offer the expertise and execution power needed to scale, without the distractions or long-term commitments that can pull you out of ‘Founder Mode.’ That's what we do at AspireSix. We live in Founder Mode! #FractionalLeadership #FounderMode #Startups #GrowthHacking #Leadership

𝐓𝐨𝐝𝐚𝐲, 𝐰𝐞 𝐦𝐚𝐝𝐞 𝐚 𝐭𝐨𝐮𝐠𝐡 𝐝𝐞𝐜𝐢𝐬𝐢𝐨𝐧!! We terminated one of our employees for the first time since starting this startup, and it weighs heavily on me. People often perceive managers as cold or heartless, but the truth is, these decisions are incredibly difficult for us too. We are not just responsible for the success of the company; we also care deeply about the well-being of our team. As an employee, I used to perceive managers as lacking empathy, especially when it came to tough decisions like terminations. However, after experiencing the other side of the coin, I have come to realize that managers are not indifferent to these situations. They carry the weight of these decisions and feel the impact just as much as anyone else involved. It's a tough position to be in, balancing the needs of the business with the well-being of the team. Letting someone go is never easy, but as managers, we carry the weight of tough decisions for the greater good of the business and team. Tough choices are part of leading, and while it's saddening, our responsibility is to ensure the company's success, even through difficult decisions. So, to anyone who may think managers or owners are indifferent to these decisions, know that we feel the impact too. We understand that they affect real people's lives. It's a responsibility we don't take lightly, and it's one that weighs on us just as much as it does on anyone else involved. #startup #leadership #LeadershipChallenges #founders #entrepreneurs

When I first stepped into leadership, I thought I had to have all the answers, handle all the details, and control every outcome. Sound familiar? It wasn’t about micromanaging, per se—it was more about wanting things to go perfectly. I wanted to ensure the team avoided mistakes, that everything ran smoothly, and that goals were met on time. But in trying to control it all, I hit a wall. The truth? You can’t grow a team—or yourself—without trust. Real leadership is about empowering others to own their responsibilities. It’s about letting them make decisions, even if they might make a few mistakes along the way. That’s where real growth happens. And believe me, it’s not easy. I’ve had to watch team members stumble. I’ve even had moments where I thought, “It would have been faster if I had done this myself.” But every time, I reminded myself that this isn’t about speed or perfection—it’s about building capability. Letting go has been one of the hardest lessons for me, but also one of the most rewarding. Today, I get to watch my team take ownership of their projects, innovate, and achieve incredible results. How do you build trust within your team? What steps do you take to ensure everyone feels empowered to lead in their own right? Drop your insights below—I’d love to learn from your experiences. #leadership #linkedinmarketing #marketing #digitalmarketing #startups

The CEO decides. If there is one thing a startup needs it is a clear direction. Clarity is speed and speed is a necessity. The direction might change and will very well be influenced by all founders. But in the end there has to be clarity amongst the team as to who makes a call. If a team understands and embraces this, it collaborates so much better. Why do I say embrace? Because agreeing to a commitment and actually believing it, can be a huge difference. If you don’t believe in your works direction you will not perform well even though you are doing what was agreed on. Everyone in the team has presented their thoughts and opinions. The CEOs job is to take it all in and make a call. Trust that decision. I myself feel reassured when Henry Diep disagreeingly makes a decision rather than us having to argue for a long time. To all early stage CEOs: Take the leap. Your team wants to be lead. Even though it might seem “bossy” initially.