$20M ARR by Unconventional Tactics

Why Read: Learn effective strategies for rapid growth, including brand differentiation, broad market targeting, content marketing, fast development cycles, and competitive positioning against industry leaders.

Featuring: Stefan Maritz (@stefmarbrand), Marketing Lead at CXL

Link to Article: “The road to $200 million ARR: How ClickUp bootstrapped its way to $20 million ARR and conquered a crowded market with unconventional growth strategies.”

Key Concepts and Tactics:

• Differentiate on Brand:

  • Point: Focus on building a strong brand to stand out in a crowded market.

  • "ClickUp set out to be the all-in-one productivity tool that solves tool fatigue for teams around the world, but product positioning and features came second in their playbook. Their success started with their brand strategy. They marketed themselves as a consumer brand instead of a B2B product."

• Cast a Wide Net:

  • Point: Consider targeting a broad audience instead of niching down.

  • "Evans also had a unique perspective on achieving product-market fit, which played a crucial role in ClickUp's growth. Rather than relying artificial market fit, Zeb believed in the power of a 'natural product-market fit.' This approach focused on creating a product that was inherently valuable and versatile enough to appeal to a broad audience.  The philosophy was that if you build a product with a wide range of applications, it will naturally find its market. This approach however contrasts with the common advice to start narrow and expand later. Instead, ClickUp cast a wide net from the beginning, confident that their product's versatility would attract a diverse user base."

• Invest in Content Marketing and SEO:

  • Point: Create high-quality, valuable content to drive organic growth.

  • "ClickUp's commitment to content marketing was an important part of their strategy. They went all in, creating a comprehensive library of resources that not only showcased their product but also provided real value. ClickUp's team has consistently published high-quality articles on an (almost) daily basis for years. It started slow but inevitably gained momentum among people looking for project management advice and solutions. From blogs and tutorials to webinars and YouTube videos, ClickUp covered all bases with a solid cadence. This strong push on content marketing not only drove traffic to their website but also built trust, educating potential users, and establishing themselves as a force to be reckoned in the productivity space."

• Adopt a Fast-Paced Development Cycle:

  • Point: Implement rapid iteration and deployment cycles to stay ahead of competition.

  • "ClickUp's rapid iteration and deployment cycles were critical to their ability to stay ahead in the competitive market. They didn't wait for perfection before launching new features or updates. Instead, they adopted a mindset of building fast, releasing often (sometimes even daily), and iterating based on user feedback. This approach allowed them to be incredibly responsive to their users' needs, quickly addressing issues and rolling out new features that kept their user base engaged, loyal and growing."

• Directly Challenge Industry Leaders:

  • Point: Position your product as a better alternative to established competitors.

  • "ClickUp's aggressive competitive approach wasn't just about highlighting their features—it was about confidently telling potential users why they should pick ClickUp over the industry leaders. They openly compared themselves to competitors, and made bold public claims about offering more value, more features, and a more comprehensive solution. This approach worked because ClickUp had built a product that could back up their claims. They didn't just rely on marketing hype—they delivered on their promises, which won over users who were frustrated with the limitations of other tools. The freemium, product-led model allowed them to lure users in an let their product do the rest. Stealing a massive chunk of market share in only a few years."

The 10 Rules of VC Fundraising

Why Read: Learn crucial fundraising strategies, including investor relations, effective pitching, honesty, competition knowledge, and authenticity. These insights can significantly improve their chances of securing venture capital.

Featuring: Jason M. Lemkin (@jasonlk), Founder and VC at SaaStr

Link:“The 10 Rules of VC Fundraising — That Many Founders Just Miss”

Key Concepts and Tactics:

• Understanding the Impact of Existing Investors:

  • Point: Maintain positive relationships with current investors as their opinion can significantly influence future funding rounds.

  • "If your existing investors have a strong brand and aren't positive on you, it can much harder to raise. At a minimum keep them in the loop. Don't just ignore them after they write a check. The converse is also true. Your existing investors are often your best source of leads for the next round of funding."

• Ensuring CEO Leadership in Pitches:

  • Point: As a founder, always lead the pitch to VCs yourself rather than delegating to other team members.

  • "It has to be the CEO that pitches the VCs. It just has to be. Don't send your co-founder or your "COO" or your CFO or whatever. For most investors, that's almost an immediate No."

• Crafting an Impactful Initial Pitch:

  • Point: Focus on making a strong impression in the first 20 minutes of your pitch, as this is when the initial decision is made.

  • "The initial VC decision is made within 20 minutes of the first conversation. Make it exciting, speak with data, and get to the point. The initial Yes, Maybe or No decision is made within 20 minutes. So save slides 20–200 for questions and back-up."

• Maintaining Honesty and Transparency:

  • Point: Always be truthful in your presentations; if you don't know something, admit it rather than making up information.

  • "Making stuff up is death, or close to it. If you don't know the answer, just say that, it's fine. But make something up that the VC knows the answer is otherwise … that's almost always a No right there."

• Mastering Knowledge of Competition:

  • Point: Thoroughly understand and be prepared to discuss your competitors.

  • "You have to know your competition cold. Every great salesperson and CEO does."

• Crafting Effective Cold Outreach:

  • Point: When using cold outreach, ensure your email is concise, data-driven, and compelling.

  • "Cold outreach works. It just has to be very, very good. Everyone reads email. But if you are going via cold outreach instead of a warm intro, make the email amazing. Simple, but metrics-filled and to the point. Hide nothing. Don't ask for coffee. Get to the point. This is your one shot."

• Demonstrating Consistent Growth:

  • Point: Show a pattern of growth over several months before seeking funding.

  • "Slow growth is death in fundraising. Just wait to raise then. If you just aren't growing quickly enough to support a venture investment, it can be better to wait and go out in a few months. At least, you need to have 3–4 good months strung together in a row to show a pattern (and hope)."

• Leveraging Existing Investors for Additional Funding:

  • Point: Keep existing investors informed to potentially secure additional funding from them.

  • "Your existing investors often save some money for a second check. Treat them that way. Most institutional investors can give you at least a little more money if you are doing OK and need it. So again, keep them in the loop. Otherwise, they won't reserve this money."

• Being Authentic in Presentations:

  • Point: Present your authentic self during fundraising pitches, while still maintaining professionalism.

  • "Be yourself. A top "sin" in fundraising is acting like someone else. Yes, being a CEO involves a little bit of acting. A bit. But overall, be yourself. Be true. 50% of fundraising is the VCs getting to know the CEO. It's OK to overindex on the topic you are most passionate about (product, sales, marketing, etc.). It's OK if the presentation doesn't look exactly like some deck you saw on Business Insider. Make it all great. Rehearse. Take it seriously. But don't not be yourself. Don't act like someone you think you should be to fundraise."