The Mentors

An indisputable character trait of every successful person is their willingness to stay persistent even when it feels uncomfortable. In this episode we discuss the growing importance of persistence in today's increasingly uncertain economic climate and how we should all get more comfortable with asking for help. 

A good way to remove negative self think when something triggers you to feel that you're asking too much of others is to remember stories of other ambitious people accomplishing great things because of their willingness to ask others for help directly. 

We discuss Barbara Corcoran's story of landing a spot on ABC's Shark Tank by following up with Mark Cuban after being rejected for the opportunity. We also talk about how Sergei got a job working for Andrew Yang's last nonprofit, Venture For America, after being rejected for a job there and following up directly with the COO almost two years later.

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Entrepreneurship is hard, but one of the basic tenets of being a creator is knowing that you can build something completely on your own terms. For Michael Fenchel, a young physics major out of Wisconsin who loved being a creator, that meant starting companies - three of them at once, to be exact. 

All three of those ventures ended up being successful, eventually leading him to start his newest company Paradox Ventures (prdx.co), a program providing personal development for entrepreneurs and leaders. But before that Michael stumbled with various failed projects, until he figured out something important - focus on adding value first, and making money second. 

In this episode Michael talks about how he was able to build one of the largest co-working spaces in Madison, WI (100State), while starting a software company that supported live music events (Prism.fm) and running product at BlueTree Network. In each example he was able to get the business off the ground and identify talent in his network that would then take over leadership responsibilities in the businesses. 

He also talks about how his experience launching and growing an education company called Breathe For Change inspired him to create a founder and leadership development business called Paradox that provides a true community for likeminded entrepreneurs that recognize the need to balance personal development with audacious professional goals.  

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From a young age we're asked - "what do you want to be when you grow up?" - implying that we have to be just one thing. Our natural curiosity may take us in unexpected directions but all it takes is an expression of doubt from someone else to stop us in our tracks. In this episode we discuss the importance of questioning self-imposed limitations and removing labels that others may ascribe to us. We discuss two main limiting beliefs that we had to overcome - the idea that we're bad at writing and the belief that we're not good marketers. 

We talk about the importance of taking the initial step to act on your internal desires, eventually removing your self-imposed labels through sustained effort that leads to the external validation you need to completely redefine yourself.

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All ambitious people, even the ones that have already experienced measurable success, feel self doubt at certain times. Knowing how to move past those feelings is critical in getting to the next stage of your journey. 

In this episode we discuss:

1) The importance of positive outcomes (wins) and other external validators

2) The value of working on what you care about and what you're good at

3) Why you should ask yourself if you're working on the right things

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All entrepreneurs have been forced to rethink their entire strategy over the last 30 days, and many are uncertain about their ability to secure funding during an unstable economic environment. In this episode we discuss what changes we're seeing in the market and how founders should approach the fundraising process now that investors are more careful about how they deploy their capital. 

In this episode you will learn: 

1) How to setup a more targeted fundraising approach

2) What types of investors are more likely to write you a check

3) How you should adjust your story and business plan to stay attractive to investors

4) What traction to focus on to raise your valuation

For more episode on startup fundraising check out our Fundraising 101 series.

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Creating a successful career is very similar to building a successful company - your outcomes are directly correlated with your execution. This week we reflect back on a story shared by Daisy dePaulis, Head of Sales at Google Cloud, who was recently featured in a free online class at School16. Daisy worked at a restaurant after going to community college for two years when she decided that her time was more valuable than the hourly work she was doing. 

In this episode we talk about how she landed a job at a tech company as an office manager, eventually moving to marketing, then sales, and how she developed her leadership skills in each role to rise to VP level early on in her career. 

We also discuss how leaders are actually discovered within companies by being willing to take on new responsibilities, coming to others with solutions and not just problems, mentoring those that need help, and learning skills on their own time.

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Being an entrepreneur means that you get to decide what you want to be an expert in each time you start a new venture. One famous example is Richard Branson, who started off running a student magazine, then a record company, followed by a successful airline and a spaceflight company. Darrell Silver made a similar move with his second company, Thinkful. 

In part two of our interview we discuss why he decided to move away from enterprise tech where he successfully sold his first business into a sector that was completely unknown to him, direct to consumer education. As before he did what he knew best - created a valuable product as quickly as possible, then figured out an effective business model for it. 

Darrell explains how him and his co-founder Daniel Friedman saw an opportunity to educate people interested in technology jobs soon after the 2008 financial collapse, and the impressive marketing experiments the team ran to create a revenue generating program in a few short months. Over 8 years they grew Thinkful to a recognized brand, eventually selling to Chegg for $100 Million to reach their next milestone - making tech based education accessible to more people.

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"Keep busy at something. A busy person never has time to be unhappy" -Robert Louis Stevenson. Today's episode is inspired by a message from Naval Ravikant, prolific entrepreneur and investor. His observation states that the physical spaces that we, typically, navigate to and from every day - be it the office, school, church, etc. - are primarily there to keep us busy. When going through a difficult period an effective way to keep negativity at bay is to create an environment where there's no time for it. 

This week we share a story from an entrepreneur that was able to create purpose for himself during this crisis by raising funding to support a network of seamstresses that create masks and other PPE for medical staff in his area. During this time what you do decide to do is not as important as committing to doing something. That alone can drastically help ease the burden of the uncertainty we're all feeling.

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Most successful founders will tell you that you can’t build a company for the purpose of selling it, yet some entrepreneurs are able to successfully find acquirers for their ventures time and time again throughout their careers. After all, that’s one of the most common exit scenarios for founders and shareholders. 

In this two part series we had the pleasure of sitting down with the founder of Thinkful, Darrell Silver, who sold his education company last year for $100 Million to Chegg, his second acquisition and second company that he founded in the last decade. 

In Part I Darrell talks about what skills and circumstances he thinks attributed to him being able to start his first venture, Perpetually, and how years of networking with others in his industry led to a successful acquisition of that business at a time when it seemed like it was destined to fail.

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The simple act of setting a big goal can change your outcomes because it defines the tasks that you prioritize in the immediate future. This week we talk about how we experienced this phenomenon first hand when we decided to launch our new education program School16. We discuss what motivated us to set a highly optimistic goal and how this led to getting over 600 signups in just a few short weeks. 

A simple framework that can be used to replicate this process is called SMART goal setting. Goals that are Specific, Measurable, Achievable, Relevant, and Time-bound. 

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