Part 3: Company-Internals Mistakes

Everything started out with good intentions… then you can’t get funding, reviews dip on Glassdoor – or worse – there’s a lawsuit. How did things get there?! Most likely, one small misstep at a time.

As you know, there's a lot going on. The goal of this list is not to add more to your plate, but to start getting you aware of things to think about, in the short - and long-term.

Business Operations

• A company is not a hobby/baby/family (!). It's a business that aims to be profitable. No one will care more about it than you do.

  • • When I first started, I took calls virtually at all hours of the day, for virtually any request; it was a lot of context-switching and complimentary sessions where founders tried to pick my brain. Now I try to bucket time blocks for when I take calls and try to pre-qualify those calls – or refer people to my blog or elsewhere, to be protective and productive with my time. It's on me to set those boundaries. It’s still a work in progress.

• Don’t Repeat Yourself (DRY): Your time is valuable! Document/record anything that you end up doing, especially the second time around, so that you don’t need to do it (yet) again (and again); this includes introductory product demos and onboarding.

  • • My blogging strategy is all about DRY.

• You don't need a co-founder (!)

Product Focus

• There are a lot of things that interest you; me too! If there's not one key focus area, it becomes harder to identify and find those ideal customers that you can sell into.

  • • It's taken me 4+ years to get here; my niche of offering "AI due diligence" is finally focused enough that that's the elevator pitch (!)

    • I see a lot of startups trying to do too many things, especially for their MVPs. (Blog) Are you a hardware company? A software company? A Data company? A Data product company? Or all of the above? When I do pitch deck due diligence, this becomes an orange flag, because you have finite resources, and with too many focus areas, you risk coming across as not knowing your customers yet, yet trying to offer them too many things – that may all not resonate. 

    • → What is your one, main focus to GTM, to start learning from your perspective customers, to help you get laser-focused on the pain point, the solution, and the pitch?

• Track customer engagement in your product before adding features to things that people aren't using. While it may seem less fun to make existing functionality easier to use – rather than add new features, by seeing what’s resonating and not with your customers, and improving their quality of life, you’ll work on the most important things for your product and will end up finding and catering to the “white hot” customer base (NFX) that will help you grow your company with product-market fit.

• Focus on learning and optimizing 1 target customer profile and 1 GTM strategy, and saturating that market before expanding into multiple products and industries. 

  • • → This will make it easier to sell the product because you will have one set of target customers, who will be your only priority.  

    • Same with your pitch deck! Focus on the one thing you're doing well now. You can add a slide at the end/appendix on how you're planning to expand once you scale your current focus.

• Have a clear onboarding strategy for your customers – and add a slide about this to your deck, even if it's in the Appendix. We really want to see ourselves in the shoes of the customers, learning what it takes to solve the pain points step-by-step.

Mentors and Advisors

Congratulations! You’ve been accepted into an accelerator and/or just brought on an advisor (or two). Here are some DOs and DONTs :) 

• Do reach out to your mentor/advisor with updates and questions; the more focused, the better. We’re here to support you; make it easy for us. I’ve never had someone ask me too many questions yet :) 

• Advisors and mentors are not free consultants – and are not IT :) 

  • • As a mentor at one well-known accelerator, I was taken aback when 2 different start-ups wanted me to implement their AI algorithms for them for free as THE scope of the mentorship. I told them that I could guide someone on their team through this, but hands-on development is outside of the mentor role – and should AI be the main focus of the time spent in the accelerator, of higher priority than customer discovery and product strategy to solve those pain points?

  • Do you really need an advisor? Or are you looking to pad the pitch deck?

    • I can’t tell you how many requests I get from founders to be able to use my name (and credentials) in their pitch deck, even after I’ve turned them down for advisory work. 

    • Please have a clear answer for me on how I can best support you and the company, how we can work together, and what contracts need to be in place to do so – before requesting that my name and credentials be included in your pitch deck.

• Do your advisors/mentors get regular updates and occasional (or more frequent) check-ins, to be able to support you better? Or are they reaching out to you every few months asking for an update?

  • • If we don’t have a 30K-foot view of what’s going on with the company (the good, bad, and ugly) and what you may need help with, we can’t help.

Company Culture

Companies are made of people who aren’t perfect; there’s no perfect company culture that works for everyone – my company included. Where are you doing well? What can be improved?

[Biggest mistake] #1 mistake I see founders make is not communicating enough, with each other – and the rest of the company. Everyone can improve on their communication, myself included. To make sure there are no surprises for anyone, strive to overcommunicate! Even if there are “only” two of you (!).

• One symptom that communication needs work is that everyone's not clear on what the immediate priorities are – and why those are the priorities, above everything else.

  • This is especially true if the initiative is a vague request for "AI". What does a scoped-down MVP look like for this, that can bring value to our customers, help you quicker learn what’s resonation (and not), and make the company money?

• TIP: Consider "just" a weekly 15-minute all-hands/async update meeting, sharing objectives for the week, month, and quarter for the company. It will help everyone with alignment!

  • • Early stage, things move fast; don't forget to catch up with the rest of your team, so that everyone's on the same page about the latest pivot and focus.

    • EX: I specifically remember one 's founder's sheer terror and disappointment to learn that the Marketing team was targeting a different customer profile than they expected; the Marketing team didn't know about yesterday's pivot.

Feedback

• Do you give immediate, constructive feedback around the behavior you do and don't want to see again? This way, you're helping someone grow and help them manage expectations about a collaboration.

• I'll ask "help me understand X (behavior)" to get a sense of their context and thinking process, instead of diving into what should and shouldn't have happened. Followed by discussing the impact of the behavior.

• Do you give kudos/shout-outs, to reinforce behavior you want to see? Is it in a forum that each of your direct reports prefers?

• Do you hold blameless post-mortems after each release/deliverable, to understand what went well, not so well, and what can be improved?

• How is the roadmap set and prioritized? Do you solicit input for opportunities from both the executives as well as from their directs? 

On-boarding

Do you have an onboarding doc, sharing not just the company mission and goals, but also whom to go to for what, where everything is, along with the goals for the first week? 

• TIP: If you don’t have one now, the next time you’re walking a new hire through the ropes, collaborate on a Google doc together, and have others weigh in! Here’s a resource that can help.

Hiring

Hiring is hard! The Biggest mistake that I see founders make (understandably because of budget constraints and hiring for an early-stage start-up), is crafting a job description that reads either like a kitchen sink of technologies they’re mostly not using (but everyone else seems to be using and hiring for) – or (on the flip-side) the needs are for one person that will be doing 3 full-time roles, across departments… all for equity compensation only. 

• Instead, when crafting the job description, share what outcomes you’d like to see the new hire help the company achieve – and what gaps on the team this role will fill. List the minimum requirements for the role and some nice-to-haves; no code challenges are required (for IC or manager roles). [HIRE blog]

• Is on-site required (and why?) or will the company be remote-first?

Technology

• The biggest mistake here is the lack of cross-team alignment across co-founders, executive team members, and departments on what the priorities of the company are – and why, to help guide the technical teams to implement the “how”.

  • Instead, often, business and technical teams are not on the same page, with a non-technical founder/executive not feeling comfortable asking questions, and the technical team ends up going down rabbit holes of feature requests that all seem equally important and urgent. Then product development goes in the wrong direction and there’s a lot of finger-pointing. 

  • TIP: Try a visualization (such as Google Drawing) as an alternative way to explain what’s going on, what’s missing, what else is needed, and what the ultimate goal is. It will help everyone get on the same page faster!

• Especially with all the AI hype, founders forget that technology should help the product grow by bringing value to consumers. We’re not adding technology to say we’re a “Tech” start-up; technology is a means to an end.

• Even if we’re a “tech start-up”, we don’t need to start by hiring developers first. Start with (interactive) wireframes/mock-ups/digital rendering first! You can do these yourself! And get customer feedback and input that much faster and cheaper.

  • • As an added bonus, once you’re ready to add functionality that requires developers (which may or may not be required), the mock-ups will help you get on the same page with developers that much faster around what you’re looking for and how it all works.

• There’s no such thing as “no technical debt”. Everything is a trade-off because we don’t have infinite time to implement every request “just so”. The code we write today is tomorrow’s legacy code.

• Everything takes longer than expected to implement:

  • • The first time, because it’s never been done before; the next time because of technical debt.

    • This is especially true if you’re not all on the same page. That can happen because you don’t have mock-ups/diagrams; it’s not clear what the end goals and outcomes you’re building towards and how are; or what the trade-offs were made and why.

• OK (and actually recommended!) to use tried-and-true technology over shiny objects, because it’s easier to hire for these skill sets and easier to maintain the codebase. This is because the “bleeding edge” technology evolves fast to find its product-market fit, making it harder to maintain. 

  • If no/low code gets you there, that’s even better.

• Build vs buy

  • • While this can be its own blog post, in short, I recommend buying everything that’s not core to your product moat, because everything you build needs to be maintained – and incurs technical debt.

    • Gergely Orosz shares an equation, for you to consider when deciding on build vs buy: 

infrastructure_cost + platform_team_cost < current_vendor_costs

where platform_team_costs can be $1M+/year for a manager to lead a team of 4-5 developers.

• • • This is especially true of EHR integrations! 

• Security and privacy risk can also be their own blog posts (!). 

  • • • In short, I don’t recommend everyone sharing the same password, especially through Slack/GitHub, to be able to access everything at an admin level. Consider 1Password vaults instead.

      • Start with security in mind from the beginning (e.g. HIPAA, HITRUST, SOC2, etc.), which will make it easier for prospective clients to say ‘yes’ to you – and to add compliant functionally piece-by-piece, from the beginning, rather than trying to re-architect later under a deadline.

• Are you also guilty of over-engineering or over-complicating the solution, when a simpler approach is better, even if it is less sexy? 

  • • • I’m guilty of this too! As you may know, I have a very simple website. At one point, everyone was telling me that it needed to be in WordPress. And maybe I should self-host it on AWS, with a Docker registry (ECR) while managing external volumes and keeping track of content via version control… Just one re-re-...-re-deployment convinced me that there should be a simpler way to make weekly edits to my website… I migrated to Google Sites, which has version control built-in, no self-hosting required – and haven’t looked back :)

      • TIP: Just because you can, doesn't mean you should; I learned that the hard way :)

      • TIP: Consider doing a “front door test” ahead of any feature development; otherwise, without a payment tied to an ask, customers are likely to suggest that all the features are just as important. Lego IDEAS is a great example of the "fake front door test": if not enough people support the project, it won't get created.

Data and AI Strategy

• [Biggest mistake] Investing $$$ into AI without a clear answer to “why AI, why now” and how it/chatbot can really help the company grow, especially if you don’t know what’s happened with customers historically. 

  • • Focus on PLG [BLOG] or PL Sales over “AI”, which is a means to an end; this will help you grow the company in an actionable way.

    • Please see Kyle Poyar’s advice in Lenny’s newsletter on PLG applied to Marketing

    • Example: United Airlines story as a result of Goodhard’s law, and no “Data dignity” 

• [Biggest mistake] Treating AI as a silver bullet that will answer all of your customer’s questions out-of-the-box as a chatbot, with code written by OpenAI to do so, with no industry or technical expertise required.

• No surveys (!): Focus on understanding the engagement in the product/app/website/etc. to have customers “show you, not tell you” what’s resonating/not and how, and where the drop-offs are happening, to measure and optimize for efficiency and the “time to an ‘aha’ moment".

  • • TIP: If you’re a platform that tracks things for your customers, don’t forget to do the same for your platform (!). 

    • TIP: Add referral links over NPS surveys, as surveys are not the only way to get data. 

    • TIP: Zapier is your friend to start collecting this.

    • TIP: The more personal the question (e.g., about money, age, etc.), the less people will reply. If you really need to do a survey, do you really need demographics, or are indirect questions about lifestyle, along with 3rd-party data (such as about zip code/IP demographics) enough? 

    • Can your survey be 30% shorter? 

• More advice on data and AI strategy

Parting Advice

• Advice for first-time founders in the healthcare industry

• Don’t forget to ask for help (!)

  • • This is especially true if you’re a part of an accelerator, where that’s part of the culture/expectation. You’re losing value opportunities by leaving the ASKs section of your updates blank.

• Scope down, scope down, scope down (!)

  • • What's the smallest step you can take now, to get you closer to your goal?

• Everything takes longer than expected, especially if not everyone is on the same page

• Cross-team alignment is hard, even with a company of size 2.

• The answer to everything is “it depends”, it depends on priorities and other priorities, outcomes, bandwidth, time to deliverable, feasibility, etc.

• Talk: Power of Data for Product Market Fit (or) Your Product Market Fit Roadmap to Escalate Your Growth (including slides and recording) 

• By mentoring yourself and learning from others async/coffee

• Art of follow-up: after I make an introduction, let me know how it went; if you expect to be late in following up, let me know. This helps build the relationship for all sides. 

There’s a story (or two) behind each of these (!); I’m always happy to meet other leaders and swap stories and lessons learned.

References

• "First Time Founder Fuck Ups — Perspective", by Kendall Miller, whose panel I shared my perspectives on -- and motivated this series of blog posts

• "5 mistakes 1st-time founders make", by Pat Walls

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