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Todd and Friel on Fundraising

John Friel

When people think of “owning their own business,” they usually either think of doing freelance wedding photography on the weekends, or raising a bunch of money and starting the next Google.

This can be a pretty significant limiting belief, since getting investors is an intimidating, stressful and time-consuming process.

But, what do you do when you need to get your company funded? And what are the trade-offs between different funding models?

I’ve raised money from friends and family in the past to cover the buildout and operating expenses of South Loop Strength & Conditioning when we took on a large lease.

And, my friend John Friel is currently in the process of applying to the well-known start-up accelerator Y Combinator for his company Art in Res.

Check out the full conversation to learn:

  • What are the incentives of investors and what are they hoping to gain out of investing in companies – and what are the trade-offs and dangers of pursuing the rapid growth that venture capitalists expect?
  • How to think about “storytelling” to investors and why some investors like to hear hard numbers and other like more narrative in their pitches
  • What are the differences between nerds, fans and utilitarians – and why do suburban dads who don’t even play guitar know so much about different tones and amps?

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from John and Art In Res here:

Show Notes:

  • [01:21] Going through the Y Combinator application process required “stepping back” and looking at the entire structure of Art in Res – rather than getting caught up in the day-to-day, in-the-weeds aspects of operating the business. It also required understanding how to “storytell” to investors – which seems to require different skillsets for finance people and venture capitalists.
  • [12:30] Why play the venture capital game rather than bootstrapping and attempting to create a “lifestyle business?” What will it take for Art in Res to grow to a scale that would justify venture capital investment?
  • [24:15] How much money should you actually raise during the fundraising process? There seems to be conflicting advice regarding being frugal – but also raising more money than you think you’ll need. And – the cognitive biases that make it necessary to game the system so that you can signal a constant and impressive upward trajectory.
  • [37:31] Thinking about the incentives of venture capitalists and why they want to invest in companies – and going down a rabbit hole to parse out the difference between nerds, fans and utilitarians. And how art collectors, coffee snobs, music gear heads and sports fans all probably follow a similar archetypal structure in terms of their enthusiasm for esoteric knowledge.
  • [53:45] How to potentially tap a latent market for art collectors – and understanding the psychology of potential consumers in order to create a marketplace on which commerce actually takes place.

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Jason Leydon (Conquer Athlete | CrossFit Milford)

Jason Leydon
Jason Leydon of Conquer Athlete and CrossFit Milford is an elite-level CrossFit coach – and, much like myself, a continuing education junkie.

I’d been looking forward to this conversation, since Jason is not only very successful in his ability to develop athletes, but also self-aware about his frameworks for coaching and his process for learning new things and applying them in his practice.

Many well-known coaches are able to get great results from athletes, but can’t really articulate how and why they do the things that they do.

Many other well-known coaches just happened to get lucky by having some freakishly talented folks walk through their doors, and have built careers on being in the right place at the right time without much actual knowledge.

Jason is the real deal, and he can articulate exactly what he’s doing and why he’s doing it.

In this conversation, we don’t just hit the nitty gritty details of developing athletes (although there is some of that). We spend a lot of time on Jason’s process for continuing to learn – and how he actually turns the things that he learns through books, seminars and courses into tangible results for his athletes and his coaches.

Check out the full conversation with Jason to learn:

  • How an identity-destroying injury started Jason on the path to coaching – and how he thinks about the psychology of athletes who have their identities wrapped up in their performance and their results
  • How Jason actually applies things that he learns from continuing education – and how he passes his knowledge on to his coaches so that they can actually apply it as well
  • How Jason thinks of the theoretical hierarchy for developing athletes – and how he picks what the top priorities are for his athletes in their training

Compliment with my conversation with Scott Young on Ultralearning for more on transferring knowledge from the abstract to the practical.

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Jason, Conquer Athlete & CrossFit Milford here:

Show Notes:

  • [1:08] What’s up with Jason’s accent? Is this how people from Milford speak? And – the sudden and shocking end to Jason’s basketball career.
  • [11:17] How to handle the sudden change in identity as an athlete who can no longer compete. And – the transition from athlete to coach, as well as the coinciding dedication to continuing education.
  • [20:21] How does Jason actually apply the things that he learns from seminars, books and courses? How does Jason think about solving tangible problems with the material that he learns – and how does he go about asking for help when something isn’t clicking for him.
  • [25:36] Connecting the practical, in-the-gym application of concepts with the theoretical learning that occurs in books or courses. Outcomes are often messy, so how does Jason figure out what’s actually working and what is just happenstance and chaos?
  • [31:14] How does Jason teach coaches who work with him to hold the same standard of coaching? Not everyone is able to learn from courses in the same way, so how does Jason pass knowledge on?
  • [37:00] How does Jason decide what his coaches need to prioritize in their coaching development? And, what lessons from learning to manage rowdy teens in a gym class are applicable to coaching adults?
  • [44:24] How does Jason manage the sport-specific needs of his competitive CrossFit athletes with their long-term development? How does a coach prioritize what an athlete needs to work on – and how does a coach create sustainability for an athlete in the sport?
  • [52:40] How to find out more about Conquer Athlete and the Conquer Athlete Podcast

Links and Resources Mentioned

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Shelby Lermo (Vastum | Ulthar)

Shelby Lermo
Shelby Lermo plays guitar for Vasum and Ulthar, and used to oversee the tangled web of death metal, interviews and conspiracy theories that was Illogical Contraption.

This conversation was a real pleasure for me, since I’ve known Shelby as an “online friend” for probably close to a decade, and have long admired his work from afar.

For those concerned with the stagnation of the extreme metal underground, we discuss possible iterations on the form of death metal outside of the contemporary postmodern juxtaposition of seemingly disparate genres or the rehashing of the past through “old school death metal.”

For those concerned with their ability to follow through on creative projects, we discuss Shelby’s discipline surrounding creativity – including scheduling time to create, separating creating and editing, and balancing multiple different projects.

For those concerned with conspiracy thinking, we discuss the allure and the dangers of conspiracy theories, as well as the mechanisms that have pushed conspiracy into the mainstream.

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Shelby, Illogical Contraption, Vastum & Ulthar here:

Show Notes:

  • [01:12] The process of making internet friends before social media, and the tangled web of content that was Illogical Contraption.
  • [09:17] The evolution of music discovery and communication in the underground from tape-trading to music blogs to Spotify – and how Shelby thinks about consuming music vs listening to music.
  • [19:58] The stagnation of the death metal genre, and how to think about composing outside of the standard idioms of the form.”
  • [24:21] Shelby’s creative process for multiple different projects, and the differing levels of collaboration between different projects.
  • [29:35] Where can death metal go next? Do the popular styles of metal in the underground follow cyclical patterns (ie thrash -> old school death metal -> technical death metal)? Will anyone create a new form for underground metal that isn’t just a postmodern hodgepodge of varied styles and instrumentation?
  • [40:48] Being disciplined regarding creativity: scheduling time to create, not waiting for inspiration, and separating the process of creating from the process of editing
  • [48:10] The allure of conspiracy theories – and why you shouldn’t believe them, as well as the surprising “mainstreamification” of conspiracy thinking.
  • [59:00] Implausible beliefs are a signaling mechanism for in-group loyalty, which can create feedback loops that increase the strangeness of conspiracy theories.

    • [1:05:05] Shelby’s favorite interviews from the Illogical Contraption podcast

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Jake Rhodes (BearKomplex) & Jason Yule (Boxstar Apparel)

Jake Rhodes + Todd Nief + Jason Yule
We’ve got Jake Rhodes from BearKompleX and Jason Yule from Boxstar Apparel and Harbor Park CrossFit on the podcast.

I met both of these fellows when they exhibited at the inaugural South Loop Games in 2016.

This episode isn’t just for CrossFit geeks, since we dig into the ways that Jake and Jason think about building a market for their businesses in a complicated and dynamic fitness landscape.

The nuances of balancing promoting competitive CrossFit and whether that detracts from the mission of health and wellness is tricky to unpack, and Jason and Jake have some interesting perspectives from working with every day people in CrossFit affiliates as well as being involved with sponsoring high level athletes and the CrossFit Games themselves.

Check out the full conversation below to learn:

  • How to balance a complicated marketplace where some people are intimidated by elite athletes and others are inspired by elite athletes – and how to find the sweetspot for different business models
  • How to make sure your business isn’t just a vanity project – and how to figure out how to actually solve problems for people and lean into those problems when you find them
  • What Jason and Jake think of the new Sanctionals structure – and how they plan to make the new structure work for them and their business models

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Jason, Boxstar and Harbor Park CrossFit here:

Check out more from Jake & BearKompleX here:

Show Notes:

  • [1:37] Jason’s feelings toward Wisconsin always being paired with some sort of nod to cheese – particularly within the CrossFit Games.
  • [4:03] Marketing in the CrossFit world must find balance between the mission of improving health and wellness for those who feel intimidated by the sport, and the showcasing of ‘freaks’ doing muscle ups and handstand walking. By focusing on the elite athletes in the sport, folks who are curious to try CrossFit can be intimidated and put off from going to the gym.
  • [11:10] CrossFit is its affiliates, not its one weekend each year where the best athletes perform. There’s a place for showcasing the sport’s best athletes, but stepping away from making those people the whole CrossFit image is important in recruitment of more ‘everyday’ people.
  • [15:24] Businesses need to figure out how to retain customers – BearKompleX can’t only target those who are ripping their hands for the first time forever, and the focus begins to shift more toward high-level athletes as the business progresses.
  • [17:53] People view elite athletes as role models – people who they strive to be like, whose gear choices influence their own gear choices, etc. It grants companies credibility to have the support of high-level athletes. Those who are newer to CrossFit had to see an ad in their box or a cool video (with a high-level athlete as the face of the brand) and want to improve their athletic ability through gear to buy product, though. As time goes on, Jason and Jake have moved their companies away from focusing on the over-saturated elite athlete field and instead toward focusing on the average athletes who are influencers within their specific CrossFit community.
  • [29:00] The goal of being able to compete in the sport of CrossFit is more attainable now, whereas competing at Regionals was previously the goal of the most elite athletes. The changes to the Games structure have affected athletes immensely – they have to be able to handle unpredictability as a piece of the ultimate test, along with the fact that they could devote their lives to CrossFit just to fly across the world and run 400m.
  • [37:45] Will someone like Brent Fikowski struggle to compete with the new structure of early cuts at the CrossFit Games? One bad workout can send athletes home early, and it makes it more challenging for outliers in body size to compete in the sport. And why is the stereotypical elite CrossFit athlete so different than the stereotypical elite athlete in other sports?
  • [45:14] Jason and Jake’s companies have to establish strategic marketing plans. Placement at events is significant (years ago, they hustled for a main vendor spot at the South Loop Games), along with having the resources to now have representation at sanctionals worldwide.
  • [53:44] The vendor floor is very saturated and companies struggle to break even with giving away free gear on top of paying a high price to have a spot at events.
  • [57:47] Online traffic spikes for a few weeks after a company is present at an event, which could be due to spectators returning to their boxes and showing off their new gear. Giving out discounts doesn’t produce much increase in purchasing but the chance of having referrals in the future makes it worth it.
  • [1:03.58] Priorities change as the Games structure changes – global expansion tactics, prize giveaways with partnerships, and continuing to find further affiliate retail space is essential. Successful worldwide representation is a struggle, but having affiliate owners get on board with carrying gear in their boxes is as well.
  • [1:15.11] More on Jason and Jake: social media accounts, opinions on quality Wisconsin beer, and the story behind BearKompleX’s name.

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Scott Young (Author of Ultralearning)

Scott Young

I’ve long been a Scott Young fan from my early days of reading blogs (miss you, Google Reader), so I was thrilled to get the chance to interview him about his new book Ultralearning. 
As a relentless consumer of information and a sometimes autodidact, I’ve found Scott’s blog to be very insightful in terms of approaching new projects and learning skills like coaching and coding without going through a formal educational process. 
With the current ubiquity of information – including entire college curriculums, endless video interviews with world-class experts, and entire industries of online courses – we should be able to learn just about anything we want. 
However, as anyone who has either attempted to learn a new skill or, God forbid, teach someone else a skill has experienced, learning is really, really hard. 
How can we actually transfer what we learn from theoretical lectures and books to real-life application? How can we practice skills in a way that makes us better at the skill itself – not just at random drills?
Check out the full conversation with Scott to learn:
  • Why listening to lectures, watching videos and reading books doesn’t tend to translate into applicable learning in most areas – and what to do instead so that you can actually transfer the things you learn into real-life practice
  • How to find the right balance between practicing the skill that you’re learning and doing drills – since some drills don’t translate effectively but only practicing the full skill can prevent you from improving on weaknesses
  • What really separates those who are willing to self-educate from those who aren’t – and why the common barriers (“I’m not smart enough,” “I’m not talented enough,” etc.) aren’t accurate

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

Listen Here

Check out more from Scott here:

Ultralearning

Show Notes:

  • [1:50] Scott seems to understand that learning is most successful in an environment of doing and not in one of reading, lecture attendance, and video watching. However, he’s published a book about learning – so what exactly is its purpose and why did he choose to write it?
  • [4:21] There’s a lot more to learning than simply practicing, as certain skills seem to involve endless amounts of practice while others have more apparent, speedy transfer. Learning becomes more difficult when the type of practice performed deviates from how the skill is used in a real-life setting. Scott gives some examples of when these transfer problems arise and how transfer problems can arise even in learning about theoretical ideas.
  • [8:46] Directness and actual application are significant in order to learn all skills, but the order in which they’re performed matters. A learning strategy is likely transferring effectively when exposure to a skill is direct prior to performing any sort of drill and, once drills are introduced, it becomes important to return back to those situations of direct exposure regularly.
  • [13:01] Skills can be built up individually while lacking functionality outside of largely abstract situations, meaning that drills must be specific and relative to real performance of the skill. Feedback on those drills (and, generally, on performance of the skill being learned) shows to be a nonessential piece of the learning process.
  • [20:12] We can get knowledge into our heads, but accessing a learned skill isn’t done by pulling out a ‘saved’ memory from the brain and feedback is self-generated through realization of what is not able to be recalled – that aspect of retrieval is vital to performance of any skill, making the sophistication of recall more effective than repeated exposure.
  • [24:38] Studies may not be representative of all populations since skills vary so greatly in context – amount of acquired knowledge and ease of retrieval positively correlate, and sample sizes tend to be small. Giving learners opportunities to apply what they’ve learned can be a step toward bridging the gap in education where people review and ‘understand’ concepts but cannot seem to make any real change behaviorally.
  • [25:54] Experience is one of the many reasons experts perform better than novices at almost any skill – an expert’s experience in a particular skill allows them to chunk things together and to see prior patterns, obvious mistakes, and recognition of solutions to problems more readily than a novice, who likely attempts to piece together a multitude of individual parts of a larger concept.
  • [33:13] Learning a skill in order to solve problems rather than to simply know the information and to have it ‘stored’ can improve one’s ability to transfer. Autonomy is a necessity though: being able to apply a skill that you don’t really want to use is unlikely, no matter what super effective strategies or level of established intelligence or personality traits are present. Anyone can learn almost anything if they want to.
  • [43:04] Many people have negative experiences with learning and associate learning struggles with failure. Once you know how to put together a puzzle, it isn’t a puzzle anymore, but confidence and persistent engagement are keys to keep trying at that puzzle.
  • [53:10] Knowledge decay isn’t as serious as many believe because large ideas are retained – making a habit of performing physics problems or speaking in a particular language can help in maintaining those learned skills, but even more abstractly reminding yourself of formulas that exist can be helpful.
  • [57:38] Attitudes surrounding learning are the difference between either merely knowing about many concepts and drowning in self-doubt or having the confidence to succeed in complicated areas of work such as ultra learning. Can we make it prestigious to be a motivated self-educating person?
  • [1:04.35] Being able to copy someone else’s behavior or learn how someone else performs well at a particular skill by being able to watch and communicate with them about the subject can enhance and expedite the learning process. However, it’s possible that this is true in skills with more clearly defined ‘rights’ and ‘wrongs.’
  • [1:14.10] How to get Scott’s book if you want it. And you probably want it. And you probably also want to check out some more Scott content. So here’s how to get all of that.

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