My standard answer to "How did you achieve that?" is "Luck".
Luck = Preparation + Opportunity + Execution.
Product & Startup Builder
Startups help us adapt to a changing world
Startups are simply the best vehicles we’ve come up with to deal with a rapidly changing world by applying first principles thinking, creativity and the scientific method to adapt to, and fix what’s broken.
Data needs UX
Data without value added UX is simply stored potential energy. It’s not enough. L
Pay attention to the details
The details matter. Getting them right can be the difference between conveying a subconscious sense of credibility - or not. Pay attention to pixels, colors, margins, voice and all the things that "don't matter"
Vision requires kindred spirits
Vision is having a prescient, almost fully formed sense of something you want to see in the world and then pulling the future into the present. Manifesting thoughts and hopes about a better way of doing things into reality.
Success requires almost every kind of skill imaginable. People skills, creativity, engineering, project management, invention, business acumen and so much more. Most of all it requires optimism and abundance thinking.
This kind of force of will can scare those who don't understand how or why this is possible.
In pursuing this journey, finding kindred spirits who's skills and insights can compliment your own is not only delightful, it's essential.
Pay for good help
There are a lot of hidden fees and charges in life. Little taxes and tips that often go unaccounted for. By far, the largest one of these is wasted time.
Ironically, time is the most expensive and precious resource we have. Both as individuals and as leaders of companies.
Do the things you love, do things that are high leverage and productive, spend endless time with loved ones, watch and read things that inspire you - but try to avoid choosing the cheapest option or the menial chores over getting the best service and professionals to help.
What you’ll spend in cash you’ll make up for in quality of life, momentum, and leverage.
Don’t over-index on feelings
Most people live very practical and pragmatic lives. They go to work and do the job they’re assigned.
There are two other kinds of people, though.
1) There are aspirational people who demand that they work on specific types of projects and problems. Big and impactful things that make them feel excited, important and inspired! This is typically a positive thing - but it can sometimes become unbalanced and lead to a situation where they are unable to execute on pragmatic, commercial things. It leads to a kind of execution paralysis.
2) There are other people who fail to act (or act well) because they feel afraid. They procrastinate or self-sabotage. This is due to a wide range of reasons that they rarely even understand themselves - but irrespective of the reason, it ultimately also leads to execution paralysis.
I suspect, in both cases, these people could benefit from recalibrating the role of “feelings” in their lives.
Part of crafting a successful life requires that you don’t over-index on feelings.
It might sound harsh, but In some cases, they need to harden up and be an adult. They need to look at the world with sobriety and meet the market (and it’s challenges) where it is, not where they wish it to be.
This is not to say that the aspirational people have to give up on optimism and ambition, only that the most effective way to achieve their optimistic goals is typically through very pragmatic and incremental means. Of course, the trick here is to understand where the line is, and have the right balance of impatience, stubbornness, and pragmatism. A difficult but critical balance to strike!
This is also not to say that afraid people can simply have their fear absolved - but rather that they need to act bravely to break out of their shell to provide for themselves and their families.
Product is all about good choices
What Is the the actual problem? This should be very specific and hopefully involve specific pain that can be quantified in dollars and cents of waste and inefficiency.
Who is your user and who is your partner? I’m seeing a lot of startups conflate these two things lately.
What is the exacted behavior (particularly for mvp)? Ive always seem companies trying to boil the ocean here. I’ve been guilty of it myself many times.
What is the point of differentiation? What is the marketing message? Be specific. Better, cheaper, faster. Pick 2. It typically can’t be all three.
At the beginning, you can’t be everything to everyone or no one will get it or care.
I’m a big tv and movie nerd so I watch a lot of behind the scenes content about them. Movies and directors also talk a lot about choices. A good movie is usually the result of a series of very good, and very consistent choices.
Just like product. They’re both art.
Your product experience should be obvious and easy to use
A good product shouldn't require a training manual or even that much text to be initially useful to a user.
The trick is to have clean and clear UI/UX metaphors that seem obvious, great "clean slate" experiences that nudge the user to do key things when they first log in and in-line tips for what to do next (just 1 or 2 sentences at most). In this way, users learn how to use the software organically.
Tips, tricks, help and knowledge base should only be available for some advanced functions or to handle edge cases.
What are some of the best examples of this you've seen in the wild?
Business People are from Mars, Academics are from Venus.
They are worlds apart.
Neither is better or worse (and both are desperately needed in our society) but it’s an interesting challenge when they try to cross into each other’s field.
Where academics seem to be much more concerned in differences and intangibles, business/product are much more concerned with generalities and tactics.
Where academics are interested in describing the world, business people are more interested in affecting it.
Where academics are interested in consensus building, business people are much more interested in finding hard facts and acting decisively to affect change.
Where academics work on the timescale of years, business people tend to work at the scale of quarters.
How do you know when you're ready for channel partnerships?
I come across a lot of startups who have a go-to-market strategy predicated on sales and marketing partnerships with partners.
The reality is, however, that in an early b2c business, If you can’t sell your own sh*t then it’s unlikely a partner can do it for you.
Partners are usually a great way to spend endless hours in negotiation and ongoing alignment struggles only to see a meddling success when the partnership is executed.
Even then, all they usually do is magnify your own process. So if your process produces poor results then a partnership will just multiply that out. 0 x 10 is still Zero.
Instead, figure out how to tell your own story with a gorgeous website, explainer video, self-serve onboarding and training flow and more. Then figure out how to scale it with low hanging fruit like ads, content marketing, mailing lists, etc.
Then, and only then, lightweight co-marketing partnerships might be useful to supercharge these activities. Deep integrations should typically be left until later.
Consistency Is The Bedrock of Effective Execution
Consistency is the bedrock of effective execution. Be wary of people who are sometimes amazing, but often not dependable or consistent in their behavior.
They are analogous to an abusive relationship. They give you just enough hope that things will improve and then they let you down.
The amount of time and energy you spend trying to manage their feelings and their behavior can be better spent replacing them with someone more consistent (and therefore more effective).
At best these people are unreliable and distracting, at worst they are toxic and dangerous.
Further, getting rid of them can actually boost team morale because colleagues see that bad behavior is not tolerated and their own consistent efforts are recognized and valued.
Make the hard decision and move on quickly.
Do A Little Research Before Getting Started
It’s more fun to start designing and building an app than doing some user and market research first.
Unfortunately, though, that can be a very expensive mistake - both in terms of time and money.
Before starting, be sure to talk to (and survey) potential partners, competitors, customers etc.
Lean into meetings
"You're always very engaged in meetings"
A startup exec I've been working with said this to me recently.
She then went on to ask "Is it because, as an external advisor, you feel like you have very short windows to add/prove value?"
My answer:
The truth is I've always felt the need to be super leaned in to meetings. I've never felt like I could coast/relax at any stage in my career.
Why?
When I was very young (15-22) I was the youngest person in the room - trying to convince 50+ year olds to do this "technology thing" my way.
When I was slightly older (20-30) running my own startups, I felt like every day and every decision was life or death. I was deeply invested and felt the weight of the world on my shoulders to come through for my team and my investors.
When I was at Uber, I was surrounded by some of the smartest and most experienced people in the world at their job. Combined with the fact that I felt like I had a real opportunity to make a difference at scale, meant that I had no choice but to be wide awake!
And now with my Advisory work, as she suggested, I feel like I have very small windows to really contribute/come through for the founder and the startup.
It's interesting because I'm also increasingly realizing I've been at a disadvantage my whole career due to my lack of caffeine intake!
In any case, I had always assumed everyone felt fully engaged for pretty much every meeting.
Engineers Make Terrible Product Managers
Before you light your pitchforks, hear me out.
Entrusting the same individual with both engineering and product management roles is akin to having your quarterback also act as your head coach—it dilutes focus and compromises excellence in both domains.
Product management is a discipline of prioritization and vision. It's a game of chess where you're perpetually thinking three moves ahead. The role demands you to be a master of the 'what,' 'when,' and 'if' decisions, to navigate stakeholder politics, and to have an instinctive understanding of market dynamics. You're not just picking battles; you're defining the war strategy, marshaling resources, and ensuring morale is high enough to see it through.
Contrast this with engineering, a domain steeped in problem-solving and execution. Engineers are the vanguards of the 'how,' diving deep into codebases, algorithms, and data structures. They inhabit a realm of tangible solutions and immediate challenges, often reaching a 'flow state' that is antithetical to the interrupt-driven nature of managerial roles. Engineers are the infantry who scale the hill and plant the flag, all while the product manager is scouting the next strategic high ground.
The mental models, responsibilities, and skill sets required for each role are not just different—they're often diametrically opposed. While synergy and constructive tension between these roles can drive innovation, conflating the two often results in diluted focus and suboptimal outcomes.
Yes, engineers with a knack for big-picture thinking can transition into phenomenal product managers. But requiring anyone to wear both hats concurrently is not just impractical—it's a disservice to both the individual and the product. Specialization isn't just a nice-to-have; it's often the key to achieving excellence.
You Get What You Pay For
In most cases, you truly get what you pay for.
Time is often the most precious thing of all. I find myself willing to spend more and more money to save time or improve the quality of the time I spend.
Whenever I balk at the price of something premium, my beautiful wife reminds me "Would you expect a company to pay a recent grad the same amount they pay you to do the same job? Why not?"
She's right. Paying to fast-forward to the future - especially for a company - can be the difference between wasting enormous amounts of capital, life force and time on a failure and winning the proverbial lottery.
Hire great people. Listen to them. Ask them the right questions. Hustle.
Software Doesn’t Sell Itself
You need a strong Product Marketing, BizDev and Sales org to drive demand. You need to have them coordinate and be lead (via influence) by Product (not the other way around).
Pitch Decks Are Not Just For Investors
Often times, startups put off creating a pitch deck until they need to raise capital from Investors. Even then, they usually see it merely as a necessary evil in the process of fundraising. However, I've found that putting together a pitch deck can be a critical tool in ways that go far beyond fundraising.
How?
Because you (as a founder), your team, customers, partners, and other key stakeholders also need strong, clear and concise narratives that help get everyone excited, aligned and moving in the right direction.
For founders: A pitch deck forces you to turn often vague notions and visions into a structured, reasoned narrative.
For customers and partners: Developing strong, reusable decks allows you to construct a strong, consistent story that unfolds naturally and gets continuously updated to cleanly handle all objections. This process allows you to scale your core message across all salespeople. Ideally, the deck mirrors and fleshes out what's on the website and other self-serve materials.
For the internal team: The right kind of decks/meta-narrative that is updated and presented on a regular cadence empowers everyone to act and make good decisions without "the boss" in the room.
Opportunity Cost Is Not Soft Or Abstract - It's Expensive
Opportunity Cost might be hard to measure, but it is not a theory or a soft abstract idea.
On Google it is defined as "the loss of potential gain from other alternatives when one alternative is chosen.
The example they give is "idle cash balances represent an opportunity cost in terms of lost interest"
So, in simple terms, the money you leave in savings cost you whatever additional profits you could have made by investing it more cleverly in stocks or property etc.
Opportunity cost, however, is not just found in clearly defined scenarios where you can measure the alternative route retrospectively and do a calculation to figure out how much you lost. It's also felt in an infinite number of small decisions and procrastinations you might make every day.
Pushing a meeting to tomorrow. Passing on some hard work due to laziness or emotionality. Not following up with someone when they offer to introduce you to someone that could be helpful. Not following up when an introduction is made. Not taking or making a key investment. Staying in a small town when a different geography might suit your needs better.
On and on
I've been guilty of this many times. Most weeks. In fact.
My constant struggle, though, is to recognize the countless opportunities to optimize my costs and maximize my effective execution through life.
Bad Deals Can Be Leveraged Against Each-other
Be careful about being too opinionated about the kind of deals and opportunities you want and being too quick to reject ideas that at first appear "wrong".
Opportunities can be leveraged against each other and sometimes the best ideas come from the places you least expect.