Tag Archives: entrepreneur

Time to Try Being an Entrepreneur?

Good people, friends and former colleagues, are losing their jobs as big insurance companies lay off staff. The sliced tether to the mothership has some considering making the jump to insurtech. As a co-founder in the insurtech space with a corporate background, I’ve been getting a lot of calls, and answering the same set of questions: What is the startup scene like, who is hiring, how to get started?

These are logical questions. I even have some decent answers.

These are also the wrong questions. They’ll help you find a job, but they won’t help you understand if you’re going to be excited to get out of bed in the morning or whether an entrepreneurial job slowly crushes you into desiccated powder.

The right question isn’t about logistics – it’s about the internal transition you’ll need to make, and whether you want to live that change.

The right question is: Who do I need to become to thrive in insurtech? (Or really, any corporate to entrepreneurial transition.) 

By thrive, I don’t mean start a unicorn. If we knew the steps to do that, 75%-plus of venture capital funds would not fail to make a profit for their investors. I also don’t mean wantrapreneuring – turning not doing into a career. Wantrapreneuring is skating from meetup to meetup, asking for lots of advice about what to do (then pushing back with a strong opinion of how it should be done, all the while not… doing).

I mean, doing the work. Finding an idea. Talking to customers. Convincing a co-founder or two and a team to join you. Or joining the team. Designing the product. Checking the font on every piece of customer communication. Figuring out why your freaking payroll vendor’s system doesn’t just WORK. 

And enjoying it. Coming into yourself in this space. Feeling like every challenge stretches you in a new direction. All the while handling the emotional extremes (which I guarantee are rawer and realer than corporate).

So, having had a corporate career before becoming an entrepreneur, here’s my read on the person you’ll need to become:

A shipper, not a soother

You know all those meetings to get opinions on a project before you actually start it? Aimed a little at understanding what your colleagues know, and a lot at tamping down later aggressive politics from people who feel left out? 

Just stop. 

Draft something, share it with your teammates, tear it up and make it better with their feedback and SHIP IT! 

The scales tip the other way here – the issue isn’t that you might offend by putting something on paper, it’s that you’ll never get to your destination if you don’t complete anything. (See wantrapreneur, above).

See also: COVID-19: Technology, Investment, Innovation

I promise you it’s leftover corporate-induced anxiety that’s preventing you from shipping. And you 100% need to find a way to force through it in the entrepreneurial environment. So ship the pitch deck, the blog post, the story, the code. Relentlessly focus on your own output. 

(Also, if you don’t write it down, or type it, or draw it, or record it, it doesn’t count. In your head is not done. So do it.)

A no-seeker, not a yes-orchestrator

You know the pre-meetings? The ones you do with your boss’s seven peers to get their input and objections before the big leadership meeting? Your goal is to avoid a no from the big boss, so at least you can keep moving. 

That’s not a model for a startup. 

Of course you should get lots of feedback (mostly from customers), and of course you should take your partners’ politics into account. 

However, the biggest gift in startup life is a quick no. 

The biggest gift in startup life is a quick no. (I said it again – this one took me too long to learn.)

And it’s amazing how many people won’t have the decency or understanding to give it to you. A maybe is not a yes. A maybe does nothing but eat up runway. When you’re small, you’re surviving on a shoestring and updrafts of hope. You need to find all-in, strong-yes partners. 

And if you’re working hard for the yes that’s not coming, these aren’t your people. Sorry. 

A lightning rod, not a moderator

In corporate life, being someone with a “strong personality” will show up in your performance review. “Tone it down,” they say. “Watch the humor,” they say, until you realize you’ve risen in the ranks by sanding down every corner that makes you, well, you. Your personality, your opinions and your willingness to argue something from the heart are the cost of fitting in. 

In the startup world, nobody funds boring. Nobody joins boring. Nobody takes a chance on boring. Average gets you nowhere. Inoffensive is a lack of conviction. 

Be prepared to own your ideas, your journey, your very self and argue them strongly. Don’t play to the crowd. Better to irritate a few people if it means pulling the ones who can help you into your slipstream.

A doer, not a delegator

Early stage, there’s just too much work and nobody to do it. You can’t set up half your payroll system, design just the principles of a user experience or draft an outline of a letter to a customer – these aren’t partially done – they are an absolute waste of time precisely because they are incomplete, and therefore unusable. 

You can’t delegate completion when there’s nobody to delegate to. Do your work all the way to the end. Let go of the perfection of corporate life and the 87 rounds of reviews, and content yourself with a customer letter you think you’d understand and with a quick proofreading. 

Oh, and delegate complete tasks, not fragments. You need a team that can also finish their work.

See also: Step 1 to Your After-COVID Future

Transition means change

I don’t buy the arguments that people are either successful in corporate environments or in entrepreneurial environments. That’s accepting a world in which none of us can learn and grow, and in which we’ll never succeed at anything we didn’t try in our 20s. It’s nothing but a package of hubris and negativity all mixed up together. 

It is true, though, that corporate and entrepreneurial environments test us in different ways. If you have a corporate job and you want to work at or start a startup, can you find a job or can you start a company? Of course you can, given time and resources. 

But can you thrive? You need to be willing to change.

Becoming an entrepreneur is just that, a becoming.

Entrepreneurship strips away our masks, for founders and for team members, both. The fate of the business is in your hands. Your work stands for itself. You stand up for yourself. 

So, don’t overweight your thinking to whether you can find a job in the entrepreneurial world. Think about who you’ll need to become to thrive in that space. Does your heart sing with delight when you think about becoming that person? 

You, and the people you will work with, deserve that.

The Entrepreneur as Leader and Manager

Entrepreneurs are doers. One of the strengths of successful entrepreneurs is that they get things done. However, relying solely on their own capabilities is limiting.

We only have so much time, energy, creativity and intelligence; it is a finite game. To realize the fullness of our potential, we have to harness the time, energy, creativity and intelligence of others. We need to be playing an infinite game.

To do so, we must learn to lead and manage.

In this complex and ever-changing world in which we live, we typically are dependent on others to get the results we want. As an entrepreneur grows his or her business, the interdependencies multiply. Entrepreneurs have to trust others — and other people have to trust them.

See also: 6 Tech Rules That Will Govern the Future  

The starting point is leadership. My friend and colleague Dr. Herb Koplowitz defines leadership as follows:

“Leadership is the ability to set a direction and coordinate the actions of others in implementing it.”

Leadership is primarily concerned with vision and strategy. Vision is the direction toward which you want to take your business. Strategy is the clear plan of action to get there. Management is concerned primarily with accountability and authority. The challenge for many entrepreneurs is that they lack clarity around their vision; they lack strategy to build the right structure; and they have never learned how to exercise authority or hold people accountable.

For the entrepreneur, the ability to create highly productive working relationships that can fulfill their vision depends on three factors:

  • Effectiveness: Doing the right things to reach their strategic goals.
  • Efficiency: Doing things right to optimize the use of resources and to reduce costs.
  • Trust: Creating a positive working environment where people feel safe, respected and valued for their contributions.

As a leader and manager, it is important to take the time to develop and implement a business plan that includes:

  • A well-articulated vision (where do you want your business to be in five years?)
  • A clear strategy to reach that vision (what needs to happen to fulfill your vision?)
  • A formal organization structure designed to implement your strategy (who and what do you need to support your strategy and achieve your vision?)
  • Staffing and managerial leadership practices to maximize effectiveness, efficiency and trust (how do you need to transform the way you lead your business?)

See also: Incumbents, Insurtechs Must Collaborate  

To take your business to the next level, you need to be a leader and a manager.

5 Pitfalls to Avoid for Intrapreneurs

Entrepreneurship is not for everyone, especially in the traditionally complex and conservative insurance business. Honing skills as an “intrapreneur” enables success in a large corporate environment while also developing the mindset to take the leap as an entrepreneur. An intrapreneur is very much like an entrepreneur, except an intrapreneur is an innovator and change agent within the confines of a traditional corporate environment.

Having been through the trenches and formerly serving on the leadership team of two major insurance organizations, becoming an intrapreneur is, unfortunately, easier said than done.

Intrapreneurs are driven employees who can harness ideas and clearly articulate their vision in a way that energizes the organization. Intraprenuers operate at the intersection of experience, ideas and insight. They innovate or facilitate innovation by building capabilities focused on dramatically changing the customer experience.

Ideas Are a Dime a Dozen

The challenge for most organizations is not a shortage of ideas but rather the shortage of intrapreneurs who can bring ideas to life and effectively execute on them to deliver sustainable competitive value. One study published in the Harvard Business Review found that, in a firm with 5,000 employees, there are at least 250 natural innovators; of these only about 25 are great intrapreneurs who can build the next business for your organization.

See also: Insurance Innovation: No Longer Oxymoron  

Intrapreneurs have an unusual ability to operate at the intersection of experience, ideas and insight. Within the confines of a traditional corporate environment, these are typically individuals who have a broad view of the business (or businesses), as opposed to someone whose experience has been focused on a singular business unit or discipline. In addition, intrapreneurs do not operate alone but are masters of recognizing the importance of aligning strategy, culture and leadership to create sustainable value. Without this, they are just another employee with a good idea and good intention operating alone in a corner office or cubicle.

  • To better understand what makes a successful intrapreneur, perhaps it is best to explain it from the perspective of the pitfalls to becoming an intrapreneur. These pitfalls can be viewed from the intersection of strategy, culture and leadership. An open culture and effective leadership team is essential to nurturing the proper environment for an intrapreneur to flourish. Because I often get questions on how strategy comes into play with regard to facilitating innovation, in my experience I have found it most helpful to discuss it from the perspective of the pitfalls to avoid. To that end, I will focus on five strategic pitfalls to avoid and how a leader can effectively go from just having ideas to becoming an engine for innovation.

The Pitfalls to Avoid in Becoming an Effective Intrapreneur

It all starts with strategy — the integrated set of choices of how the business will achieve its objectives and deliver value to customers.

  • Problem and market not clearly defined: The intrapreneur cannot reply to nor expect an organization to have a preexisting framework to prioritize its external threats or weaknesses. Taking the initiative to think about this on your own time via an exercise like a SWOT analysis (strengths, weaknesses, opportunities, threats) puts an aspiring change agent in a position to be seen as a person who takes initiative — and one who is not only looking at problems from an internal micro perspective but from an external macro view as well.
  • The customer experience is an afterthought: A recent trend in organizational development is the change of the role of customer service to “customer success” or “customer happiness.” It’s typical particularly in larger organizations and consultancies to get so wrapped up in internal change initiatives that the external customer is almost an afterthought. If you are an intrapreneur with customer-facing responsibilities, establishing a set of key performance indicators (KPIs) for customer success provides a way to test and measure improvement. Approach this from the mindset of being the new leader of an organization — what metrics would you put in place to move the organization from vanity metrics such as call response times to more meaningful KPIs such as net promoter score (NPS) and qualitative data like testimonials?
  • No delivery mechanism to bring innovation to market: An idea is not effective until a framework for execution is put in place to test, prioritize, execute and track any internal innovation initiatives. Consider appointing a champion of this initiative who is not only an innovator but is someone with a track record of delivering results. This doesn’t mean going through the expense of simply bringing in a consultant. A simple Google Sheet can be the start of listing the tasks, resources, time required and cost of going to market with an internal innovation. Share this within the organization to give other innovators an opportunity to comment and contribute, thus creating further momentum and interest in seeing these initiatives to fruition.
  • A bloated road map: Taking a play from the Lean Startup framework, an established organization need not waste time mapping out a “five-year plan.” The next step is to break the initiative into bite-sized chunks that can be validated and to then proceed to the next stage. For example, suppose one of your innovations is to enable a live-chat service on your enrollment website. Traditionally, this would involve conversations with compliance, IT, marketing and sales — all with the assumption that people will actually use it. Instead, validate it before you even build it by polling existing users if and to what degree they would prefer live chat to your existing email- or phone-based support. If the results are significantly in favor of the chat initiative, then you have just successfully validated a real need without spending a single dime.
  • No clear path to revenue: One final and perhaps most important characteristic about successful intrapreneurs is that they have a clear view of how the business will make money and how profits will be delivered and sustained. Few characteristics make intrapreneurs more prepared to move into the world of entrepreneurship than this resolute focus. This is often one of the most difficult challenges of being an effective innovator, particularly if you are entering an entirely new market or vertical or are developing a new product.

See also: Innovation — or Just Innovative Thinking?  

There is no better testing ground to becoming an entrepreneur than first testing the waters in a responsible way within your own organization as an intrapreneur. From the leadership team down to the customer service new-hire, innovation should be not another top-down initiative but an organic exercise where employees are encouraged — and rewarded — for thinking outside of the box.

5 Things Sailing Taught Me

Most entrepreneurs don’t just want to be entrepreneurs—they have to be entrepreneurs.  

As a driven entrepreneur in the insurance industry, you will encounter both challenges and rewards far beyond that of the average employee. Navigating these ups and downs can be as challenging as steering a ship through a storm on the high seas, but I’ve done both—and lived to tell the tale.

The lessons I learned sailing the seas have served me just as well on land. Here are five tips about entrepreneurship that sailing has taught me:

  1. Know the terminology

In sailing, understanding boating terms like aft, starboard and leeward is vital to working with your crew and operating your vessel. The same is true in business. If you can`t speak the language of your clients and your competition, your next deal may get lost in translation.  

Attending conferences and taking courses are both great ways to learn new terms and highlight that there`s a reason why you’re the expert.

  1. Use trends like the wind

When sailing, jibing and tacking help you manipulate the winds to steer your vessel in the right direction. In business, trends are your winds, and you need to understand which direction they`re heading. Take a few minutes every day and bring yourself up to speed on the latest global and local trends.

Aggregators like Feedly or SmartNews, along with social media feeds, keep you on the cutting edge and aware of which way the wind is blowing.

  1. Learn when to tighten or ease the sheet

The sheet is a line or rope used to adjust a sail against a force of wind.  

In business, you need to think about when to tighten or loosen your budget and your business’s growth in line with your sales cycle and market forces.

Markets ebb and flow, and your business will, too. Tracking these fluctuations over time will help determine the ideal time to launch marketing campaigns and hire employees, or to tighten the purse strings.

  1. Adjust quickly and wisely to a changing climate

The weather can change in an instant when you’re sailing, and you need to know how to use the sails to compensate, navigate under tough conditions and capitalize on whatever’s thrown at you. It`s not much different when you`re a leader in business.

Like the weather, business is always moving and changing. Whether you`re steering your ship at sea or driving your business on land, it takes experience and at times raw courage to weather a storm. See each storm as a chance to gain experience for the next one and know that sometimes you simply need to batten down the hatches – and wait it out.

  1. Be a decisive captain

It can take an entire crew to run a sailboat, but they won’t work effectively without a captain calling the shots. The crew rely on your vision, tenacity and experience to guide their actions. Without this direction, no one will know which way to travel.

As the captain of a ship or a business, you spend your days adjusting your sails, guiding the crew and at times navigating dangerous waters. If you’re on the verge of starting a business or taking it in a new direction, remember one thing above the rest – always keep your hand on the helm and keep in mind:

The pessimist complains about the wind. The optimist expects it to change. The leader trims the sails and sets a new course.

Dear Founders: Are You Listening?

Since my last post, “Distribution is 80% of your problem,” I have had the opportunity to speak in-depth with several terrific start-up founders about some of the incredible things they are doing and why things are not going so well. Several of their stories remind me of another big lesson I have learned over the years: We entrepreneurs often mistake “listening” as “waiting to talk,” until it’s too late.

A Little Knowledge (About Your Users) Is a Dangerous Thing

All the stories have a similar theme: We launched our product, and we got 10,000-plus users (or 100-plus small paying customers) using unscalable ways. Now, we are not sure of what to do next.

One founder I communicated with had talked to hundreds of her paying users and managed to convince herself that her market was women who want to make sure their kids don’t get too much unsupervised screen time. We talked to the company’s users and discovered that, in fact, the core group that loved the app were working women who want to keep track of their kids and know they are safe after school. Whenever this start-up had spoken to its user, it heard the answer it wanted to hear, not what the users were saying. The lesson learned here was about waiting to tell users what they “should” be doing with the app.

Another app — one that got to 20,000 users quickly with a small amount of seed money — found, once we dug deep, that fewer than 150 of their users were active weekly. The start-up had no idea who these 150 users were or what, specifically, they were doing with the product. After 20 user interviews, we discovered the start-up’s core use case was far from what the company thought it was and that the product was too hard to use. For far too long, the start-up was convinced its technology would change the world, especially because 20,000 users seemed to be using the product.

A third, B2B-focused start-up I recently spent time with has more than 100 paying users but has stalled growth and usage numbers. When I asked the company to tell me who its users were and what pain point it was solving, I kept getting back a laundry list of features and user personas instead. When the company dug deeper and spoke to users, it found that, of the 27 features, users are using two and that no one had discovered the three the company thinks are the real killer benefits. We realized the company’s model needs to shift away from “my users are using the wrong features and should have discovered the ‘right ones.'” As a start-up, you don’t get to tell users what scenarios and which features they should use your product for; consumers will tell you by using whatever they find useful.

Apple May Not Need to Talk to Users, But the Rest of Us Do

As a founder, you start with a hypothesis. You have all these incredible suppositions on how you will change the world with your product. You may think you can get away with: “My users do not know what they are doing. I will tell them what they should do. It works for Apple (or so goes the myth) so it will work for me — let’s just ignore users.” Believe me, those kinds of companies are black swans. For the rest of us, our users matter—who they are, what they use our products for and what they ignore.

This is for two basic reasons:

  1. Product/Market Fit: Unless we know and understand our users (or potential users), our incoming hypothesis of the value our product provides is literally that —a hypothesis. Sure, some people may not get it, and some may just dismiss it. But without a group of people who buy into the value we hypothesize that we can provide and who agree to become ecstatic users of our product, we probably did not have a real hypothesis to begin with, just a supposition that is wrong.
  2. Go-to-market: The more detail we can find out about users, the more we can figure out how to go after them in a tight, focused way. Going after moms who want to limit unsupervised screen time is very different from attracting busy working moms who really want to know where their kids are after school. The two are different products, have different features and have a different go-to-market.

One potential red herring during the early days comes when you manage to attract a chunk of users quickly. You can easily get deluded by the numbers — they’re like inventory, they hide a lot of problems. You convince yourself that what you’re doing can’t be wrong if 20,000 users think you’re right. The fact is that these 20,000 people do not think you are right ;  you somehow managed to “get” them, and they experimented with your product hoping to find something of use. 200 of those users might think you are onto something, but you don’t know who those 200 are. If you understood what those 200 really like about your product, you might be able to find the next 20,000 users who are really right for you.

What to Avoid When You Do Decide to Talk to Users

  1. Don’t defend what you have built and try to convince them you are right;
  2. Don’t keep coming back to your vision and what will come later or focus on product features they should be using;
  3. Don’t make a sales pitch about your company and yourself, make it about them and their real reaction to your product—even if it means you have to throw everything away and start over again.

If you do not do these things, you have not really listened to your users—you have just waited for your turn to talk and convinced yourself you understand your users.


Here’s a framework I have developed over the years about when and how to listen to users:

The First 500 Users

Those first 500 users are the most important people in your journey. You need to do more than just talk to them, you need to build a solid relationship with them — they are the foundation of your product.

In my previous start-up, a career marketplace, I personally introduced my early adopters to friendly hiring managers at many companies and helped them land a job. A lot of those early customers are now my Facebook friends. Some of them even became our ambassadors and had equity in the company.

Those first users add immense value. They  validate your hypothesis, refine your ideas, recruit more users and test new features, on top of a whole lot more. And they are also very forgiving to defects, crashes, bad user experience (UX), everything.

I used to schedule as many phone calls with them as I could. In every conversation, I would first show what we were working on (in detail) and get their feedback. I would then open up  and  ask about what they were doing with the product, why they chose it over others, how they found it added value, what related issues they had that we could help with, among other questions. I logged every conversation.

Listening Is Hard to Do—For Founders in Particular

Most of the time when we think we’re listening, we are actually just waiting for our turn to talk. Here are three reasons why:

  1. We are always busy talking — to ourselves. Even when we are obviously talking to someone else, we are also internally talking to ourselves. So listening genuinely — muting your internal conversation and giving someone your full attention — is hard.
  2. For founders, listening genuinely is harder. Most entrepreneurs have their product, features, ideas and vision so deeply ingrained that, when they talk to users, entrepreneurs are always defending things they find users having problems with . (“But you didn’t see the profile page; the settings let you change this,” “There are so many cool things you can do, didn’t you see this feature?,” “We’ll get to that in Version 3,” “Wait, no, you don’t understand, that’s where the puck is going,” etc.)
  3. It is not easy for people to articulate what they are thinking. To really understand what users are saying, you have to read between the lines. Even if you lead with your world view, you really have to listen to users’ views carefully — both what is said and what is not.

Talking to users requires real effort . Be aware of that and start focusing on your first 500 users. Treat your early adopters with special respect — make them feel special and take care of them beyond just the product.

Beyond the First 500 Users

Moving forward with your customer base requires using other techniques (in addition to real conversations) that are still important. One such tactic is talking through the product,  provoking conversations with product experiments.

An example of this would be radically changing your on-boarding — drop everything and get them in — for a small set of users and seeing what happens. Remove a feature you think is not useful and wait for users to complain. Removing things temporarily is the best way to test if they are really valuable.

It also helps to create ancillary products  ( quick prototypes )  to test value outside your core product. As you learn more about your users, you will start to see more value propositions, some that align with your vision and some that don’t.

Until you are truly convinced you have product-market fit, do not be shy about running small experiments on the side to keep testing different ideas. Use conversations to create hypotheses, and experiment quickly.

Another technique is to always ask, “What else would you want this product to do for you?” in every support email. My start-up once introduced a critical defect in our iPhone app that led to hundreds of support emails. Adding that one question uncovered several hundred feature requests, including a lot we had not thought about.

Talking to users as you scale is more than just about having conversations. Lead with a hypothesis, measure, iterate, run side experiments continuously to test.

Dear founder, do not wait to talk to your users until it’s too late.

And when you do, listen. Don’t just wait to talk.