Tag Archives: entrepreneurs

investing

The future of Pricing and Packaging with Adam Hauff of Sentinel One

The conversation centers around Adam, a marketing professional deeply experienced in pricing, packaging, and monetization strategies, particularly in the cybersecurity and SaaS sectors. Adam shares insights into his career trajectory, the significance of pricing and packaging in go-to-market strategies, and how companies evolve to adopt specialized pricing roles, especially as they prepare for IPOs or scaling phases. He highlights the complexities of pricing new products, exemplified by OpenAI’s pricing missteps, and explains evolving pricing methodologies, including cost-plus, value-based, and the emerging outcome-based pricing.

The discussion further explores how SentinelOne, a well-known cybersecurity company, approaches revenue growth beyond sales scaling, emphasizing reducing friction, improving customer experience, and expanding into new markets or products through self-service and low-barrier strategies.

Adam articulates how AI, specifically large language models like ChatGPT, are changing individual productivity and organizational workflows. He illustrates practical AI uses from summarizing notes, generating project ideas, conducting research, to iterative content creation. However, he also notes AI’s limitations such as hallucinations and the challenge of integrating AI tools company-wide due to approval processes.

The conversation ends on an engaging note with Adam’s humorous anecdote about using AI to explore the improbable question of how long it would take to “eat” a cast iron skillet by cooking with it, which reinforces how AI can be a powerful “second teammate” for brainstorming and problem-solving when paired with human logic and oversight.

Highlights

  • 🔥 Adam’s career uniquely blends pricing, marketing, and go-to-market strategy expertise in cybersecurity SaaS.
  • 💰 Pricing and packaging become critical roles for scaling tech startups, especially around IPO readiness.
  • 🤖 AI tools like ChatGPT amplify productivity by assisting with research, communication, and iterative content creation.
  • ⚖️ Emergence of outcome-based pricing as an evolution beyond traditional value and cost-plus pricing models.
  • 🌍 SentinelOne’s growth strategy prioritizes reducing friction and enabling self-service to expand revenue channels sustainably.
  • 🚀 Companies are still adapting to AI integration at scale; individual use far outpaces organizational deployment.
  • 😂 Fun anecdote showcases AI’s ability to engage in complex, absurd queries and collaborate interactively with humans.

Key Insights

  • 📊 The importance of specialized pricing roles during scale-up phases: Adam stressed that hiring dedicated pricing professionals often happens during late-stage startup phases or IPO preparation. This is when pricing can no longer be “winged” by founders but requires systematic strategy to optimize revenue and market fit. Many companies could benefit from introducing pricing roles earlier to avoid “skeletons in the closet” and structural inefficiencies that stifle growth. This insight emphasizes maturity in pricing as a key factor in business scaling.
  • 💡 Pricing complexity in AI products reflects the unpredictability of user behavior: Adam’s commentary on OpenAI’s $200/month pricing mistake illustrates a larger problem—when launching novel AI-driven offerings, predicting user consumption and cloud costs is challenging. This unpredictability makes pricing pilots, iterative learning, and flexible price adjustments crucial. It also highlights that cost-plus pricing, while less favored, remains an important reference point to ensure product sustainability amid scaling user demand.
  • ⚙️ Outcome-based pricing represents the next evolutionary step beyond value-based pricing: Outcome-based pricing monetizes actual results achieved rather than anticipated value or simply usage. This model aligns incentives more closely with customer success but requires clearer metrics and sophisticated tracking. Adam’s view that this approach is an evolution rather than a replacement suggests organizations will adopt hybrid pricing models before fully transitioning, signifying a gradual shift in monetization philosophies.
  • 🔄 Expanding revenue beyond traditional sales requires reducing friction and enabling self-service models: Adam highlighted ways to grow revenue beyond just increasing sales headcount, such as enabling easier product access, trials, and bundled offerings that empower customers to explore solutions independently. This strategy allows companies like SentinelOne to scale revenue while controlling costs, entering new markets or verticals with lower barriers, and creating diversified monetization “engines.” This insight is essential for organizations aiming for hypergrowth without proportional increases in sales investment.
  • 🤝 Cross-functional collaboration is key to successful pricing and monetization initiatives: Adam’s role involves coordinating pilots and rolling out pricing changes with sales, marketing, operations, and internal teams to ensure organizational alignment. Pricing is not just a finance or marketing function but requires enterprise-wide buy-in, reinforcing that monetization strategy is foundational to broader go-to-market execution.
  • 🤖 AI significantly enhances individual productivity while presenting challenges for organizational adoption: Adam uses AI tools daily for note summarization, idea development, and project research, improving efficiency and creativity. However, organizational adoption lags due to concerns over AI hallucinations, content quality, and governance. This gap highlights the need for better frameworks, training, and AI governance in enterprises to fully leverage AI’s capabilities.
  • 🎭 Success with AI tools depends on curiosity and persistence rather than immediate perfection:Adam emphasized that users who gain the most from AI experimentation usually display curiosity and iterative usage, including trial and error. This mindset applies universally; AI’s limitations mean early abandonment forfeits its potential benefits. His approach of personal experimentation, including creative projects like writing children’s stories, demonstrates how familiarity with AI’s quirks fosters meaningful adoption.
  • 💬 The analogy of AI as a “second teammate” underscores its complementary role in decision-making: Adam described AI as both highly knowledgeable yet occasionally “stupid,” echoing the idea that AI needs human collaboration to check and guide its outputs. This interplay is crucial for realizing AI’s benefits while managing risks related to accuracy and context. It suggests the future workplace will emphasize symbiotic human-AI partnerships rather than replacement.
  • 😂 Humor and creative use cases reveal AI’s potential beyond standard business applications: The cast iron skillet experiment humorously highlights how AI can engage with intricate logical puzzles and help humans think through unconventional problems. Such playful interactions foster better understanding of AI’s capabilities and limitations, encouraging innovative use while serving as a reminder that AI requires human judgment to avoid absurd conclusions.
  • 📈 AI’s role at SentinelOne spans both product innovation and internal productivity: The company integrates AI and machine learning directly into cybersecurity offerings, enhancing customer SOC analyst efficiency. Internally, employees experiment with AI tools to improve research, data synthesis, and business operations. This dual application signals AI as a strategic asset not only in product development but also as a productivity multiplier, essential for tech companies competing on innovation.
  • 🧩 The evolving role of marketing now includes monetization strategies and revenue enablement:Adam’s broader remit beyond pricing packages involves creating new revenue channels that do not rely solely on increasing sales personnel, reflecting the shifting marketing landscape. Marketing intersects deeply with product packaging, pricing, partner enablement, and customer experience, positioning marketers as pivotal in holistic revenue growth strategies.
Overall, this conversation paints a comprehensive picture of how modern pricing and packaging intersect with marketing, AI adoption, and strategic revenue expansion in a high-growth, tech-driven environment. Adam’s practical and candid insights offer a roadmap for organizations navigating pricing complexities, AI integration, and sustainable growth initiatives in today’s dynamic market.
Ai

Podcast with Dan Sanchez on AI Marketing, AI Slop and the future of AI Agents

🚀 Just had an incredible conversation with Dan Sanchez—a marketer, podcaster, and AI power-user who’s pushing the boundaries of what’s possible with AI in content and marketing.

We started off light—turns out Dan released a full music album on Spotify using AI tools like Suno and ChatGPT, despite not being a musician. That led us into a much deeper discussion about how AI is transforming the way marketers work—especially for those who want to 10x their output without 10x-ing their headcount.

Dan broke down AI in marketing into five distinct use cases:

  1. AI as Co-Pilot – think planning, thinking, troubleshooting, organizing. From writing emails to managing your health goals, AI can be your smartest executive assistant.
  2. AI for Content Creation – yes, blogs and posts, but also infographics, videos, and even music.
  3. Hyper-Personalization – dynamic experiences tailored to individual customers at scale.
  4. Conversational AI – inbound chat, SMS, even phone. It’s replacing SDRs for good reason.
  5. Analytics & Forecasting – still early, but fast-evolving and game-changing.

We talked at length about AI as a co-pilot, not a magic button. The insight? AI is like having 10 subject-matter experts at your side—branding, copywriting, strategy, fitness, relationships—but you have to orchestrate them. Knowing how to prompt well is still useful, but Dan argues we’re evolving from “prompt engineering” to “clear thinking and communication.” And honestly, he’s right.

A few big takeaways for marketers:

  • Prompting matters less than it used to. You don’t need to be a “prompt wizard”—you just need to be specific and intentional.
  • Context is everything. Use AI tools that let you organize projects and retain context over time (like ChatGPT folders or custom GPTs).
  • Video podcasts are a content goldmine. Use AI to repurpose long-form audio/video into high-impact LinkedIn posts, clips, blogs, and newsletters. Start with real insight, let AI scale it.
  • Avoid “AI slop.” If your content feels like warmed-over blog stew, it probably is. Start with original thought and let AI help with structure, formatting, and tone.

We even dove into the difference between using AI for brainstorming versus automation. Automation (like API workflows) still demands engineered prompts—because consistency matters. But when you’re thinking, learning, or creating? AI thrives in messiness, as long as you guide it.

Dan summed it up best: “AI doesn’t replace marketers. It replaces the marketers who don’t use AI well.”

This episode is for every marketing leader, agency founder, or solo creator trying to scale smarter, not harder. If you’re still on the sidelines with AI, this is your wake-up call.

#MarketingAI #GTM #AIinMarketing #Podcast #ContentMarketing #LLMs #ChatGPT #AIworkflow #B2BMarketing

Artificial Intelligence

AI is already reducing the number of software developers needed

1 Comment

I have a network of about a thousand entrepreneurs, founders, and small business owners who read my blog posts daily of the 114K subscribers to this blog. I get a chance to ask them questions and poll them once a month or sometimes more often.

Over the last few months as part of a project, I have been polling them frequently and asking them about AI and the impact at work. Most of these are software entrepreneurs (a smaller number are eCommerce founders).

The poll I conducted yesterday was:

“Are you reducing the number of people you hire because of ChatGPT, generative AI and other LLM – Large Language Models”?

– generated many emails and a few phone conversations.

One particular example was telling which a friend related to me yesterday.

The company has 10 people, 8 of them are developers. The CEO of the company provided subscriptions to ChatGPT ($20 / month) and GitHub Copilot ($19 / month) to all the developers and mentioned that he won’t hire for another year and instead the developers could use the AI tools to do their job.

  1. The CEO is happy since he hired one fewer person
  2. The employees were happy since they are getting a chance to use new tools (AI prompt engineering looks good on the resume now).
  3. The HR person is happy since they don’t have to hire and train, onboard, and recruit a new person

All around goodness.

AI is already starting to reduce the number of jobs. It is just doing it a little slowly.

Software entrepreneur prompt NightCafe AI generated
Entrepreneurship

The top 12 books about startups, funding, building lasting companies by sales

There are 100’s of books written by Silicon valley founders and leaders on the topic of funding, starting companies and building organizations to last. The top 10 in terms of number of copies of books sold are

  1. The Lean Startup by Eric Ries (2 million copies sold)
  2. The Hard Thing About Hard Things by Ben Horowitz (1 million copies sold)
  3. Zero to One by Peter Thiel (1 million copies sold)
  4. The Innovator’s Dilemma by Clayton M. Christensen (800,000 copies sold)
  5. The Startup Owner’s Manual by Steve Blank (700,000 copies sold)
  6. The Art of StartUp by Guy Kawasaki (600,000 copies sold)
  7. Crossing the Chasm by Geoffrey A. Moore (500,000 copies sold)
  8. The Startup of You by Reid Hoffman and Ben Casnocha (400,000 copies sold)
  9. The Lean Product Playbook by Dan Olsen (300,000 copies sold)
  10. The Startup Owner’s Finance Book by Steve Blank and Bob Dorf (200,000 copies sold)
  11. Venture Deals by Brad Feld and Jason Mendelson (150,000 copies sold)
  12. The Angel Investor’s Handbook by David S. Rose (100,000 copies sold)

Here is a one sentence summary on each of these books

  • The Lean Startup by Eric Ries: Build a minimum viable product (MVP) and test it with customers as soon as possible.
  • The Hard Thing About Hard Things by Ben Horowitz: Be prepared to make tough decisions, and don’t be afraid to fail.
  • Zero to One by Peter Thiel: Focus on creating new markets, not competing in existing ones.
  • The Innovator’s Dilemma by Clayton M. Christensen: Incumbent companies often fail to innovate because they are too focused on their current customers.
  • The Startup Owner’s Manual by Steve Blank: The four steps to starting a successful business are customer discovery, customer validation, customer creation, and customer scaling.
  • The Art of StartUp by Guy Kawasaki: Build a strong brand, tell a compelling story, and create a passionate community around your product.
  • Crossing the Chasm by Geoffrey A. Moore: When you’re launching a new product, you need to first focus on early adopters, then move on to the early majority.
  • The Startup of You by Reid Hoffman and Ben Casnocha: Your career is like a startup, and you need to be constantly learning and growing.
  • The Lean Product Playbook by Dan Olsen: Use a lean approach to product development to reduce risk and increase your chances of success.
  • The Startup Owner’s Finance Book by Steve Blank and Bob Dorf: Understand the financial side of your business so you can make informed decisions.
  • Venture Deals by Brad Feld and Jason Mendelson: Learn how to negotiate venture capital deals so you can get the best possible terms.
  • The Angel Investor’s Handbook by David S. Rose: Learn how to become an angel investor and help early-stage startups succeed.
Entrepreneurship

Book review: Zero to One – Peter Thiel

“Zero to One” is a book that challenges entrepreneurs to think beyond incremental progress and instead aim to create something new and valuable, to go from “zero to one.”

Written by Peter Thiel, a Silicon Valley entrepreneur and venture capitalist who co-founded PayPal and was an early investor in Facebook, the book presents a contrarian view of business and innovation.

Zero to One Book

Thiel argues that competition is overrated and that startups should aim to create monopolies, as they provide the most value to both the company and society.

He also stresses the importance of having a clear vision for the future and the ability to execute on that vision, as well as the need for a strong team.

Created with Nighcafe AI

He argues that startups should focus on creating something new and unique, rather than simply competing in existing markets.

The Hollywood script summary!

If I were younger, created by Dall-E

FADE IN:

We open on PETER THIEL, a brilliant and eccentric entrepreneur, sitting in his office in Silicon Valley. He’s deep in thought, staring at a whiteboard covered in equations and diagrams.

PETER THIEL (V.O.) The world is changing faster than ever, but progress seems to have slowed down. We need to find a new path to innovation.

We see a montage of Silicon Valley tech companies, all working on incremental improvements to existing products. PETER THIEL shakes his head in disappointment.

PETER THIEL (V.O.) We’re stuck in a world of competition, where everyone is fighting over a slice of the same pie. What we need is a new philosophy of innovation. We need to go from zero to one.

PETER THIEL starts writing furiously on a notepad, scribbling down his ideas. We see glimpses of his past – co-founding PayPal, investing in Facebook – as he talks about the importance of building something new and revolutionary.

PETER THIEL (V.O.) We can’t just copy what’s already been done. We need to create something that’s never existed before.

We see PETER THIEL giving a lecture to a group of young entrepreneurs, urging them to take risks and think big. He talks about the power of monopoly, and how creating a unique product or service is the key to success.

PETER THIEL Competition is for losers. If you want to create something truly great, you need to find a way to be the only one doing it.

We see PETER THIEL mentoring a young startup founder, pushing her to think beyond the bounds of what’s possible. We see the company grow and succeed, thanks to PETER THIEL’s guidance.

PETER THIEL (V.O.) The world needs more innovation, more creativity, more boldness. It’s time to go from zero to one.

FADE OUT.

Entrepreneurship, Tips

How to be a good writer- Amazon style

When I worked at Amazon, most of my days were spent writing or reading narrative style documents. Most everyone has heard of the 6 page narrative that Amazon prefers over PowerPoint presentation. I read many newsletters but most do not measure up to the quality and usefulness of an Amazon document.

Most newsletters writers are not story tellers and that’s what causes me to unsubscribe quickly.

While there are a lot of resources on how to write like an Amazon person, I have yet to see a good writeup on the difference between plots (fiction) and structures (non-fiction) style writing.

Fictional stories have plot

Fiction stories have plots. They are formulaic. Here are some examples.

  1. The Three-Act Structure: This is one of the most common plot structures, which involves dividing the story into three main parts – the setup, the confrontation, and the resolution. The first act sets up the story and introduces the main characters and their conflicts. The second act is the confrontation, where the characters face challenges and obstacles, leading to a climax. The third act is the resolution, where the conflicts are resolved, and the story ends.
  2. The Hero’s Journey: This plot structure was popularized by Joseph Campbell’s book “The Hero with a Thousand Faces.” It involves a hero going on a journey or adventure, facing challenges, and transforming as a result. This structure typically includes various stages, including the call to adventure, crossing the threshold, facing trials and tribulations, and returning home transformed.
  3. In Medias Res: This plot structure starts in the middle of the action, with the story unfolding through a series of flashbacks or other narrative devices. This structure can be a bit more complex than other structures but can be effective in creating suspense and intrigue.
  4. Episodic: This structure involves a series of related, but somewhat self-contained episodes or stories. This is often seen in TV shows or anthologies, where each episode has its own arc but contributes to a larger overall story.
  5. Linear: A linear plot structure is a straightforward chronological telling of events from beginning to end, with a clear cause-and-effect relationship between each event.
Non fiction stories have structures

Non fiction stories have structures. They are also formulaic. Here are some examples.

  1. Chronological: This structure presents events or ideas in the order in which they occurred, from beginning to end. It’s a popular choice for biographies, historical books, and memoirs.
  2. Cause and effect: This structure explores the relationship between two or more events or ideas, showing how one leads to the other. It’s often used in books on science, politics, and social issues.
  3. Problem and solution: This structure presents a problem or challenge and then offers a solution or a way to address it. It’s a common structure for books on self-help, business, and leadership.
  4. Compare and contrast: This structure explores similarities and differences between two or more topics or ideas. It’s often used in books on history, culture, and politics.
  5. Listicle or guidebook: This structure presents a series of tips, steps, or pieces of advice on a particular topic. It’s commonly used in books on self-help, cooking, travel, and other practical subjects.

As a newsletter writer, your goal is to get people to read, not just subscribe. I would highly recommend you pick a style that suits you and follow that structure consistently.

Open rates are mostly meaningless except for advertisers. Hang time (time spent reading) is a more useful metric of how useful your content is.

Marketing, SaaS

ChatGPT is the Swiss-army knife for your creative work

While specialized tools for each job are important, most people have a Swiss army knife with them. That’s for 80% of the job for most people.

ChatGPT is the Swiss Army Knife

Last week over 100 Generative tools were released – from resume builders to Bloomberg Finance GPT.

List from Generative AI page on LinkedIn

While most people I believe will still use ChatGPT, each role (engineers will still subscribe to CoPilot from GitHub, and marketers will likely subscribe to ChatSpot from HubSpot) will have their special tools.

I liken this to the similar explosion of eCommerce and B2B sites in 1997 – 2000.

Amazon would help you buy everything, but collectors loved eBay, and overstock still exists as does Zappos for shoes and Zulily for fashion.

Frequently Asked Questions

  1. Why can’t Google do better than ChatGPT? They have better resources, lots of talent and money.

Google can do better, will do it and is already doing this. The same can be said about when Google first came and Microsoft had more money, resources and talent but still got upended by Google in search. ChatGPT has distribution quickly (over 100 Million users). While another AI chatbot is a click away, so is Google search. Still, billions of people use Google over Bing because it is better.

2. Do you need more than one chatbot? Is there room for Bard and ChatGPT?

Most people will use one or two chatbots (or more) depending on their need. Most people like to have a second opinion, especially when it comes to non factual questions. Meaning, when questions are subjective in nature, you need to get another opinion.

Many datasets (such as LinkedIn or Facebook) will not share their data with either Google or OpenAI. They might roll out their own chatbot. The folks that need it will use them.

When Netflix first came, most people did not think they needed more than one streaming service. Now we have 10+ in the US alone with over 10 Million users and the average user has 3 accounts or more.

eCommerce, Entrepreneurship, Learning

How can you spot trends before they become “mainstream”?

While the best approach to be ahead of the curve is to invent a trend, many people dont have the luxury of time from their day job to invent or keep on top of trends within their industry or overall.

While many people are good at observing and keeping their eyes wide open, most people would like “another pair of eyes”.

I interviewed 5 people who spot trends within B2B, Marketing, eCommerce and consumer internet to understand their process. 4 of them now pay for a trend spotting SaaS product.

My initial thesis was that Venture Capitalists and seed investors are more likely to spot trends because they get so much inbound interest.

Turns out, most VC friends were asking me for trends in Platform Engineering, SaaS Control plane and headless eCommerce engines.

If you have the time, the process for following trends is simple:

a) Follow influencers & analysts in the space you are interested in,

b) track Google Trends, Trendsmap (Twitter Trends), Join many Facebook groups, etc. and

c)Subscribe to newsletters, blogs and YouTube content creators.

Unfortunately that takes time as well.

In the last 3-4 years several Trend spotting SaaS websites have started as well.

I wanted to share the 5 most useful trend websites, since each of them focus on specific niches and have their own pros and cons.

  1. Exploding Topics: The site has over 15K topics and trends. They do have a few newsletter for 1-3 trends and charge $39 to $299 per month for their Pro Version.

2. Trends.vc: Is a curated newsletter with top topics within a specific niche but is also a community of people (1000+) interested in trends. You can join the community ($299 annual or $99/month).

3. Treendly is similar to Exploding topics, and bills itself as Google trends “on steroids. Pricing starts at $99 per year, but the free version is a good place to start.

4. Trend Hunter is focused on ideas, trends and captures early kickstarter campaigns as well. Pricing starts at $24K per year, so this is focused on the enterprise segment.

5. Trend Watching has a self service tool, called Trend platform, that costs $900+ per month, so it is aimed at the corporate market as well.

Of the 5, I personally like Exploding topics the most. For personal use to track specific topics and areas for our business, the tool does a good job and has sufficient coverage in technology and developer trends.

Mentors, Tips

Why LinkedIn Creator Mode is best for “temporary personal branding & campaigns”

LinkedIn has over 900 Million users as of 2023. Over 199 M of these are in the US and over 101 M in India. LinkedIn Creator mode was launched in March 2021.

A year later, over 10 Million users turned on Creator mode and 2 years in, 30 Million have turned it on. Less than 400K users, however publish weekly and fewer than 100K daily.

Creator mode offers 1/ LinkedIn Live ( video and audio streaming), 2/ Newsletters, and 3/ Follow link (instead of connect)

Having been using it for the last few months after an initial use in 2021 (Mar – Aug), there are 5 things I have learned about it. There are many articles on how to use it and why you should use it, but this post is focused on who should use it and for what purpose.

  1. I would only recommend LinkedIn creator mode if you are selling to businesses and have services that they desire. That means if you are an eCommerce company, consumer internet startup, etc. it wont give you the return on time spent.
  2. LinkedIn Creator mode (LCM) is best if you are offering services (consultants, non-fiction book authors, personal branding as a business coach, boutique small agency) as opposed to products (SaaS companies are not a good fit).
  3. LCM makes most sense if you intend to create content frequently – which ranges from daily to weekly. It is also helpful to have everything in one place – a newsletter, “Podcast”, live webinar, recorded video, etc.
  4. LCM is useful if you create content that does not drive traffic away from LinkedIn (i.e. link to your blog post, etc.) When I created content on my blog (outside LinkedIn) and posted a link on LinkedIn, the # of visits and views were < 100, but when I took that same content and posted a summary of the blog post in < 100 words, with no links and no hashtags (to test the platform), the number of views increased to > 2400.
  5. Since the content “lives” on LinkedIn, the discoverability is a lot harder with organic Google search. I took 3 articles which I ranked on the first page of Google search results organically (and have little competition for) and repurposed the content for LinkedIn, with some changes, but the LinkedIn optimized content does not show up in the first 2-3 pages of search results.

LCM makes sense if you do not want to spend money on hosting your own website, blog or podcast (which can be a cost and daunting for non technical folks, albeit easier now than ever before).

A big disadvantage of using the LCM newsletter is that you do not have access to the email addresses if you ever wish to move to a new platform (such as Substack for example).

One list of the top 200 LinkedIn creators shows most of them are personal branding coaches and career coaches.

Another angle to use is it for “temporary” branding.

Lets say you are in between jobs or taking a break in your career, or you wish to write a book, but that’s not going to be your main focus in the long term. LCM would be the best use of your time, with a low footprint, low cost approach to “temporary” personal branding or campaign.

Bottom line if you intend to be a consultant or freelancer, or offer a service (courses, tutorials, etc.) that appeals to career professionals, then LinkedIn Creator Mode may be a good option for you.