The Mentors

Quitting a job can feel exhilarating and intimidating at the same time. In a perfect world, you’re leaving on good terms and have a supportive boss that offers you future opportunities for mentorship and references.

Unfortunately, these circumstances are usually far from perfect. Many people leave their jobs because they’re unhappy, and the source of this unhappiness typically comes from the people that they work for.

There’s many misconceptions about what to expect from this process, and how to handle the conversation with your employer when the time finally comes. We start this episode with a role play, giving you a real life example of how to handle a boss that reacts horribly to the news of you leaving. A situation like this can often be fraught with emotions on both sides, so it’s important to be fully prepared going into the conversation.

We breakdown how you can anticipate questions and objections from your boss, and what to do to prepare ahead of time. Whether you’re quitting your job to work on a new business, or leaving for a better opportunity it’s important to know your rights as an employee. These tips will help you stay calm and at ease throughout the process, and remember – it’s only one conversation. Soon you’ll be on your way to a happier you.

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The best opportunities are often in the long tail where no-one is looking. This is one of the reasons why startups have an advantage over established businesses - unique strategies can be quickly tested at any time when there's no oversight or rigid processes. 

This week we talk about three stories of entrepreneurs that were able to create a seemingly unfair advantage resulting in accelerated growth. We reference a student that leveraged texting to reach parents, recap how Teespring (Episode 62) acquired their early customers, and tell you the story of how Tinder grew from 20,000 users to half a million users in one month. 

The three main takeaways for this week's 5 Minute Pick Me Up are: 

1. Be as specific as possible in defining how you will get in front of your customer
2. Go where others don't 
3. Leverage your unique domain knowledge or network to activate untapped channels

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It's hard to say no to a six figure check but sometimes your best option is to reject it. In this episode we explore three commons reasons for walking away from an investor that's ready to put money into your startup. Here are some red flags to watch out for: 

• An early stage investor that wants too much operational involvement
• An investor that gives you an exploding offer
• A wealthy individual that is making their first and only angel investment

For each scenario we point to stories from real founders that we've worked with and why their decision to walk away ultimately helped save their respective companies. While there are always exceptions to the rule we bring up these cautionary tails to help first time fundraisers make the best possible decision for their company. The allure of money can be deceiving and as with any contractual obligation the decision to accept money in exchange for equity should be considered carefully.  

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This week we tell a story of a Venezuelan med school student who opened up a burger restaurant in Spain called Goiko Grill that grew to over 40 locations and sold for €130 Million only 4 years after the first restaurant opened.

We talk about why partnering with the right people can mean the difference between hyper growth and stagnation, and what uniquely positioned this particular entrepreneur to succeed.

When you make constraints for yourself it becomes easier to be creative. For a similar reason scarcity creates resourcefulness. You learn how to solve problems in unique ways when you have fewer options available to you.

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Sometimes the questions that we bury deep inside of us are the ones that should be asked first. This is part two of a segment where we try to answer questions that we get from founders in private. Things that often only come up once we've been talking to someone for quite some time.

In this week's episode we answer the following three questions that came up in our recent conversations:

1) How do we decide who's the CEO?

2) What if I feel like I want to give up?

3) How honest should I be with my team?

We discuss how to be honest with yourself about the best choice of leader for your team, what to do first before you make the drastic decision to shut down your business, and why there's a difference between transparency with your co-founders vs. the people you employ.

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One of the greatest misconceptions about career progression is that the consequences of our choices should always be predictable and linear. It's this thinking that creates risk averse decision making for fear of irreversible outcomes, potentially closing you off to opportunities that could lead to something you can not yet foresee. Over the last few weeks we've had several people come to us expressing trepidation in making the right choice in the next step of their career. To help anyone else that might be going through this, we reshaped this question to three simple prompts:

1) What are the soft and hard skills you can learn to fill your own skills gap?

2) Where do you need to grow your network, whether it's industry or expertise based?

3) Is this next step helping you level up in a measurable and significant way?

What should also help inform your decision is the understanding that most careers today are not linear and that the old way of deciding the next step in your career does not fit the model of the new economy. 

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Every entrepreneurial success story has a strong visionary that’s able to recruit countless others to help them along the way. Being willing to ask for help isn’t only critical in the early days of building something. It can help you avoid mistakes at every level, filling any gaps in your knowledge, your network, your experience, and much more. Still, for many asking for help is not natural. It’s easy to feel like you’re inconveniencing someone while adding no value to them. Fortunately, this is mostly a false line of thinking.

We start this episode by discussing how to get over this initial feeling of self-doubt by first understanding that every successful person has gotten help from someone else to get to where they are, and by using negative visualization to realize that the worst that can happen if you ask for help is, well, absolutely nothing.

Next, we break down the most effective way to get others to help you, especially if you’re approaching important people. Start by using whatever you can to your advantage (your friends, classmates, colleagues, your expertise, etc.) and prove to others that you’re serious about what you’re trying to accomplish. Lastly, we suggest offering value whenever you can, giving examples from our past, and being as specific as possible when asking others to help you.

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If you need to do something hard start by committing to it for just 30 minutes. You can do almost anything for 30 minutes no matter how difficult it is. This is the advice that Natalie Gray got from her college professor, pushing her to finish a 3 year graduate degree in just 1 year. She later applied that advice to teaching herself how to be a designer, marketer, sales expert, and product leader. She's now the Co-founder and Head of Product at Cover, a startup that recently raised $27 million to change the way people get insurance. 

While Cover has grown very rapidly in its first four years - getting accepted into YCombinator on a prototype, getting rapid early customer traction, attracting investors, and tripling in size to 124 employees in just the last year - Natalie's story to getting to this point was anything but a straight line. 

In this episode we talk about the various career shifts that led her to teaming up with her current co-founders on a completely different business and how working on that business for two years, and then together at Shopify after being acquired, ultimately lead them to recognize a massive opportunity in insurance while on a weekend hack session at a cabin with the team. 

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Everyone's timeline is different but if you're lucky enough to identify what you're uniquely good at, it's imperative that you pursue it. This week we got to watch world renowned violinist Karen Gomyo perform at the Rhode Island Philharmonic Orchestra and after seeing our dads old documentary the next day we noticed a parallel in their very different paths.

They're passions started as internal feelings that couldn't be explained, but their calling was formed over time by external validation and unwavering pursuit despite overwhelming difficulty. This week's 5 Minute Pick Me Up explores the idea of passions and how to know if your passion is actually a calling. 

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