Category: Lessons

Startups Stop Chasing Deer in the Forest. There’s a Better Way

Lessons, Startup

I’ve been trying to explain the difference between push and pull marketing to early stage founders—and investors – for years. And finally, on a recent mentoring call, it clicked. The perfect analogy just dropped into my head:

Hunters don’t run screaming through the forest hoping to magically crash into a deer.

Why do so many startups (and brands) act like this?

Push Marketing: The Forest Sprint

Most early-stage founders default to what I’d call the “push” approach:

  • Cold emailing hundreds or thousands of people
  • Cold DMs
  • Cold calls
  • Cold everything

It’s frantic, exhausting, and wildly inefficient—like sprinting through a forest hoping to stumble into a deer. Sure, you might bump into one eventually. But is that really the best use of your energy?

I’m Guilty Too

Let me be real for a second: I’ve done this. I’ve pushed.

Sometimes it feels easier to just do something, even if it’s not the right thing. Pushing feels productive in the moment—but it’s usually just noise. Most of the time, it burns time and energy without meaningful results.

I’ve had to catch myself, take a step back, and consciously switch back to a pull mindset.

It’s not always easy. But it’s worth it.

Pull Marketing: Set the Trap, Then Wait

Great hunters don’t chase deer. They understand the terrain, know where the deer go, and set up shop. They wait. Watch. Then they take the shot when the moment is right.

That’s pull marketing.

In startup terms:

  • Hosting a podcast or blog that draws in your exact audience
  • Building a community or newsletter
  • Speaking at the right conferences (aka, where the deer are)
  • Creating useful content that attracts your ideal customers
  • Making yourself findable for the people already looking

You attract, then you act.

What Most Founders Get Wrong

I’ve seen this mistake over and over: founders spend all their time “pushing” instead of building something that pulls people in.

They forget the world has flipped. People don’t want to be chased. They want to discover something interesting. Something useful. Something aligned with their needs.

In the forest of startups, you don’t need to run. You need to learn the land, set up shop, and wait for the right deer to wander in.

You won’t catch every one. Some shots will miss. But your odds? Way better.

Outsmarting the Job Hunt

Lessons, Systems

Recently, friends and family have been asking me for job-hunting advice. Of course, I am happy to help, but I do find the request a little odd because they know that I haven’t held, let alone applied for, a traditional job since my consulting days post-college. Maybe they are looking for some inspiration that is different than the typical job-hunting advice, not sure, but I do know that my entrepreneurial experience has given me insights into hiring.

The Most Creative Approach

One memorable method was from a guy who wanted to work at CareBand. Instead of applying directly, he researched and wrote a strategic article (read the article here) about the company, offering recommendations as if he were the CEO. He sent this to me and other CEOs who he wrote about via LinkedIn or email.

I was thoroughly impressed and frankly caught off guard by this approach. It showed dedication, interest, and hard work. Although he wasn’t the right fit for us, he eventually landed a job he loved using this method.

The Most Strategic Approach

Getting a job is just a funnel, and as I have shared before the fundamentals of funnels are everywhere. A funnel is a step-by-step process with well-defined steps, conversions, and outcomes. With this strategy, getting a job is a numbers game. Here’s how to approach it:

  1. Target List: Identify companies that interest you, regardless of if they have active job postings.
  2. Network List: List your LinkedIn contacts working in interesting jobs.
  3. Connection Mapping: Note connections or introductions needed to reach a person at each company.
  4. Cheat Sheet: Prepare templates for LinkedIn and email connections (catch up, cold connect, introduction request). You will use these to copy, paste, and tweak when connecting with people
  5. Self-Assessment: Answer key questions about your skills, past experiences, and job preferences.
    • What did I learn at my last company?
    • Why am I looking for a new job?
    • What skills do I have?
    • What am I uniquely qualified to do? Where am I a subject matter expert (SME)?
    • What do I want to do?
    • What do I not want to do?

Lastly, create a google sheet to track your progress. Start connecting with people and asking for 30 minutes of their time to catch up and pick their brain about their careers, then at the end of the conversation see if they or someone they has a spot open for you. Track the way you met, date of meeting, and follow up on the sheet so you can see your progress. The goal is to have as many conversations as possible to learn about opportunities and get referrals.

Tips:

  • Be clear with your answers.
  • Create a free calendar link for easy meeting scheduling (i.e. calendly)
  • Be direct and set clear expectations.
  • Get comfortable with asking for help.

This is the most strategic and most effective way to get a job (in my opinion). I always say that you are going to get a job through talking to people, not applying with the masses. Sometimes (if you are really a catch), companies/ people will create a job for you and you will get to write your own job description.

The Least Effective Way

Applying through job websites is the most common but least effective method. I’d say 90% of people go through this process. It’s slow, competitive, and leaves you with little control. You’re just another applicant in the crowd.

It is hard to get a job today. Its a crowded and virtual market. Anything you can do to stand out and be unique goes a long way. Good luck.

What I have learned and realized about working with startup advisors, consultants and firms 

Lessons, People, Startup

You know what you are good at, what you like to do, and what you can learn to do. But there are many skills that you don’t have and you know you need them to accomplish your goals. This is where you identify these areas, then go out and find other people or companies to fill in your gaps. The process of doing this and doing it well has been a learning journey.

I have learned a lot while running CareBand and other ventures. Not only about working with people and partnering with companies but with how people work and the world works.

Without trust, all is lost

Lessons, Startup

“Why didn’t you come to us? Why didn’t you tell us this two months ago? We could have helped.” Ron (one of my investors) said.

Last week, Sam (one of my advisors) and I discussed our strategic partner and the relationship’s challenges. Sam then shared a Sam-ism (a piece of wisdom Sam sometimes shares to explain something he has learned in his 40+ year career). He said, “In any new relationship, I readily expend trust. If you break my trust, I am more cautious and go to the thinking trust but verify. And, if you break it again, the relationship is over. Then I do not trust you any further until you acknowledge your failure and apologize. Rebuilding is then possible, but it is a long road.” 

Ron and his organization have broken my trust more times than I could count in the past two years. They would promise to do or act on certain things, but then nothing would happen. When asked, it was like they forgot and just swept it under the rug, pretending like it never happened. And then, every quarter, they would ask for feedback through a survey. I was always honest in my responses, but it consistently came back to bite me. Ron and the organization’s members would either ignore the feedback or defend themselves instead of growing from it. This cycle caused me to lose trust in them repeatedly, with no acceptance on their part.

It made me feel bad like I was a terrible person. That this investor, this organization that supposedly believes in my company and me, disregards my feedback and defends themselves. I was frustrated, angry, and emotional from all of this. What was I to do? They were my investor, after all – they had a strong say in my company. How could I keep moving forward when I felt so conflicted?

…

I paused for a minute, considering how to answer Ron’s question. I could tell he wanted me to say that I was sorry and I should have come to him sooner, but the truth was, I wasn’t.

“I don’t trust you,” I said honestly. “I don’t trust your organization.”

Ron didn’t seem phased by my response. He kept talking like nothing had happened like he always does. But this time, I felt empowered by speaking the truth. No longer did I feel the anger and shame of this feeling. Instead, I felt the power of saying the truth face to face (well, zoom face to zoom face).

Ron explained how his organization had helped many other startups with this and that. He skipped right over what I said about trust and went straight into defensive mode. There was no acknowledgment, no ownership, no empathy, just attack. Pushing all the blame back to me; it was my fault.

Immediately as the call ended, I felt those strong emotions come on again. I was frustrated and angry from all of this. I took a deep breath and then another.

…

Without trust, all is loss. A relationship that is intended to support, grow, and develop falls apart under these conditions — especially one between an entrepreneur and investor. There is no room for growth and collaboration, only blame, defensive mechanisms, and a failed relationship.

This is not how trust is built. There is no self-awareness, vulnerability, or alignment in mutual respect – the foundations of a trusting relationship are entirely absent here.

As I continue to grow my company and attract new investors, I now realize that I need to seek relationships with those with a growth mindset. Investors who understood that they are not always right and who believe in mutual respect. This is another learning opportunity for me and a way for me to get better.

A hard week: bad contractor break up & lessons learned

Lessons, Startup

It’s been one of the hardest weeks of my startup journey thus far and concluded with a hard meeting. I had been anxiously waiting for this meeting for the past month. Every scenario of how it could play out occurred in my mind with all the anxiety-filled thoughts with each outcome I thought through. The actual meeting was just as hard and uncomfortable as I thought it would be. I spent so much time thinking about what to say in the meeting and how to get through the meeting that I didn’t prepare myself for how bad I would feel after the meeting.

Let me fill you in on the back story. As you have gathered, I am a technical founder and have learned to sell through my experience building this business. My process is based on all the blogs, books, and advice I have received. It also means my process is not standardized, efficient, or productive. I know that at some point, I would need extra help to accelerate the company’s growth. By the end of 2021, I knew that the time had come. So I sought a Sales and Business Development contractor to accelerate our deal volume and close additional partners. After months and months of interviewing, I finally found and hired a Sales/BD Contractor who I believed was the best fit.

This meeting I just had was the result of that contractor who had a bad breakup with the company. I will spare you (and the contractor) all the details about the relationship and how it unfolded, but I want to share my reflection on the situation and lessons learned.

Before I share, I want to reiterate that every decision I have ever made with the company is in the past. I repeatedly tell myself and believe that I made the best decision possible with the information I had at the time. This mantra clears my consciousness and gives me the space to reflect, learn, and grow, so ultimately I can become better because of it.

Lessons Learned

  1. Before hiring a Sales/BD contractor
    1. Clearly define the goals, metrics, milestones, and reasons you are hiring a Sales contractor
    2. Determine what type of selling skills this contractor needs to have to be successful. What stage of maturity are you at?
      1. A product has already been sold to a few customers and a defined playbook (defined could mean many different stages, from a few notes to exact personas to sell to, etc.)
      2. There is a product that has no playbook and needs to figure out how to sell
      3. There is a product in development, and pre-orders are needed, resulting in a lead time
    3. If you say the product is in 1 or 2., then have 100% confidence that it is. If not, say something in the pre-hiring discussions to set the right expectations.
    4. For the best results, the product should be in 1. and have already been sold by the founder to early customers.
  2. Managing and working with a sales contractor
    • Clearly describe to the contractor and ensure understanding of the steps are clear for what happens after a deal is signed
      • What blockers could arise in delivering the product to the customer promptly?
      • Who in the company is responsible for delivering the product?
      • If an order isn’t completed through the process, it takes too long, or there is an error along the way, then have a post-mortem. Talk it through with your team and fix it for next time.
    • Have a minimum of weekly sales calls to understand each deal in the pipeline in detail
      • What deals are you working on, and in what stage are they in?
      • What are the drivers for the customer? Why is the customer interested in this product?
      • What are the blockers for the customer? If you could remove all those blockers, would they sign tomorrow? What else is holding them back?
    • If issues arise, have a check-in and figure out what is happening with “Aaron Cooper’s Famous 3.”
      • The contractor understands the goal. Enough to repeat it back to you and gets it.
      • The contractor disagrees with the goal or feels negatively toward the goal.
      • The contractor doesn’t have the skillset or ability to reach the goal.
    • If an issue keeps coming up or can’t be resolved in a check-in, it is time to let the person go.
      • Don’t feel shameful, guilty, or unsure. If you have a gut feeling about the situation, just let the person go. It will save you from all the challenges later.
  3. Ending the relationship
    • Make sure the paperwork is clear.
    • Get a status report or hand off and move on.
    • Let it go, this is the hardest part, but you have to let go and let the control go. Learn from it and move on.

The Full Circle of Student Startups

Lessons

“Thank you. I am delighted and proud to have you involved. I feel like we’ve come full circle.” My old professor said in his closing remarks at our third meeting on Zoom. The first two meetings were to align the Committee on short and long-term goals and our processes. I was looking forward to the third meeting where we were going to get our hands dirty in the life-changing moments.

My Company’s Identity Crisis

Lessons, Startup

This afternoon I had a follow-up call with a prospective investor, Tom, to review our pitch deck. We were going through questions about our use of funds, exit strategy, market and sales plan, and milestones. As we were talking, I sensed that he was formulating an idea in his head. Then Tom asked me, “What is the scope of the problem you are trying to solve? What is the best opportunity to maximize investor capital? Is it to focus on the dementia and senior living market, or is the scope broader than that with applicability to drop the technology into 5 or 6 different verticals?”

Weekly Lessons – 12/7/2020 – 12/11/2020

Lessons

Engage plastic manufacturers or full-service prototyping shops early in the process when going to production. Your mechanical engineer and industrial designer can only tell you so much about your product’s type of plastic and production method. Working directly with their business development or solution engineers at these manufacturers is the best option to minimize mistakes. They have a wealth of information in terms of material, lead time, cost, etc. They will tell you what to do and what not to do for your application. They are the experts on plastics.

It’s time to start a parallel effort.

Lessons

Since March, I have been working with my team to adjust our existing dementia safety wearable to help organizations manage the risk of COVID-19. The goal was to convert the features focused around dementia monitoring to the general population focused on contact tracing, social distancing, and geofencing.

Sales 101: Get a Face-to-Face

Lessons, Startup

The investor call ended, and on cue, my partner called me to discuss.

“Sales 101, get a face to face meeting with them.” He forcefully said. “They have expertise in the industry, understand the problem, and have experience in startups. They check all the boxes.”