<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Jake’s Substack: Jake Does Biz]]></title><description><![CDATA[Building a business in public, learning it all on the way. Don’t try this at home, or do but don’t blame me.  ]]></description><link>https://www.jakew.ca/s/biz</link><image><url>https://substackcdn.com/image/fetch/$s_!k5tm!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcf66df35-58be-4040-94bc-08d971e90917_1282x1284.jpeg</url><title>Jake’s Substack: Jake Does Biz</title><link>https://www.jakew.ca/s/biz</link></image><generator>Substack</generator><lastBuildDate>Wed, 13 May 2026 19:03:51 GMT</lastBuildDate><atom:link href="https://www.jakew.ca/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Jake Winters]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[jakewca@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[jakewca@substack.com]]></itunes:email><itunes:name><![CDATA[Jake Winters]]></itunes:name></itunes:owner><itunes:author><![CDATA[Jake Winters]]></itunes:author><googleplay:owner><![CDATA[jakewca@substack.com]]></googleplay:owner><googleplay:email><![CDATA[jakewca@substack.com]]></googleplay:email><googleplay:author><![CDATA[Jake Winters]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[First Actions]]></title><description><![CDATA[It's easy to talk the talk, but here's what happened when I tried to walk the walk.]]></description><link>https://www.jakew.ca/p/something-that-didnt-work</link><guid isPermaLink="false">https://www.jakew.ca/p/something-that-didnt-work</guid><dc:creator><![CDATA[Jake Winters]]></dc:creator><pubDate>Mon, 12 Dec 2022 21:05:44 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/9b197e8a-cbdc-4e44-a21e-1185c0894254_2000x1621.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2" target="_blank" href="https://substackcdn.com/image/fetch/$s_!53B3!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!53B3!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 424w, https://substackcdn.com/image/fetch/$s_!53B3!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 848w, https://substackcdn.com/image/fetch/$s_!53B3!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!53B3!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!53B3!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:null,&quot;width&quot;:null,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:&quot;First Actions&quot;,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="First Actions" title="First Actions" srcset="https://substackcdn.com/image/fetch/$s_!53B3!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 424w, https://substackcdn.com/image/fetch/$s_!53B3!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 848w, https://substackcdn.com/image/fetch/$s_!53B3!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!53B3!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F451debe1-ba9b-42b2-8f93-4e409fc37188_2000x1621.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div></div></div></a></figure></div><p>It's easy to talk the talk, but here's what happened when I tried to walk the walk.</p><p>According to The Startup Owner&#8217;s Manual, the first step after coming up with some hypotheses is to test them. The first hypotheses to test are the Problem Hypotheses. The first step to testing a hypothesis to schedule a chat with someone who could be experiencing this problem.</p><p>The reason I chose the family law field is because my wife is a lawyer who does family law. I know from her that lawyers in this field are overworked and there's still more work to be done. I want to help her and other lawyers, and be able to build a business to help do so as a full time job.</p><p>I ran an initial interview on my wife but the results, I expect anyway, are quite biased. She did refer me to a mutual friend who might be able to be an unbiased source. So I just needed to schedule a chat with her. It would be an obvious easy win, right?</p><h3>First Inactions</h3><p>Well, next came the social anxiety.</p><p>I read up on how to &#8220;hack&#8221; the anxiety. Anxiety is a fire alarm&#8212;a call to action. To do what though? Is it perhaps because I don&#8217;t know what I&#8217;m doing? This is most likely. So I read up more and sought out more examples of problem discovery. They are few and far between.</p><p>It turns out I have very low self-worth. With the help of my therapist, we focused on my belief that to ask people for some of their time, even if it&#8217;s just to let them rant at me, even if my intention is to try to help them, is still just <em>me being a burden</em> to them. Either they say "no", because I&#8217;m worthless, or they say &#8220;yes&#8221; because I&#8217;ve guilted them into it.</p><p>So I did a lot of learning around worthiness and vulnerability. Reading about ways to tackle the shame when it does show up, so the sting of social rejection isn&#8217;t as painful. I try to truly believe that I am worthy of that time I&#8217;m asking for.</p><p>Early in November, I made a deadline. I decided to aim for scheduling the first interview by December 1st. Somewhere in between, I managed to spend three days crafting a brilliantly worded message with the simplest of asks.</p><blockquote><p>Hey [friend's first name],</p><p>It&#8217;s been too long since we&#8217;ve hung out.</p><p>It's a huge ask, I know, but I'd love your expert insight on some of the things that hinder lawyers practicing family law in New Brunswick. Would you happen to have time to grab lunch? Perhaps later this week or next week or next?</p></blockquote><p>I felt confident. For the first time since I decided to do customer interviews and problem discovery, I actually felt confident. I managed to send the message without impending dread.</p><p>Of course, that confidence wasn&#8217;t warranted. The next day I got a response. I don&#8217;t know how to take the response other than to assume it means &#8220;I don&#8217;t want to talk to you.&#8221;</p><p>I&#8217;m shattered. The only request I thought would be truly "easy" was exceptionally difficult to make and the only &#8220;sure thing&#8221; was not sure at all. This is super demoralizing.</p><p>This left me quite distressed, and considering my options. So, where do I go from here? Do I switch targets and try to find a different lawyer to interview? Or do I just give up on family law lawyers and pick an easier niche? A lot of friends have said that I should keep trying.</p><p>I think I will.</p><p>So this week, I made a list of all the lawyers I can find, ranked them by how likely they fit in the target market, how likely they are to say yes, and now I'm trying to figure out a better message to send to get them to chat. Perhaps I can make my intentions clear with a gift.</p>]]></content:encoded></item><item><title><![CDATA[The Story So Far]]></title><description><![CDATA[About five years ago, I decided I wanted to start a business.]]></description><link>https://www.jakew.ca/p/the-story-so-far</link><guid isPermaLink="false">https://www.jakew.ca/p/the-story-so-far</guid><dc:creator><![CDATA[Jake Winters]]></dc:creator><pubDate>Mon, 14 Nov 2022 00:22:07 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/95d7a0cd-d5a8-48e6-beb1-e45bf661cdcf_2000x1333.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="captioned-image-container"><figure><a class="image-link image2" target="_blank" href="https://substackcdn.com/image/fetch/$s_!gfma!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!gfma!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 424w, https://substackcdn.com/image/fetch/$s_!gfma!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 848w, https://substackcdn.com/image/fetch/$s_!gfma!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!gfma!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!gfma!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/c70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:null,&quot;width&quot;:null,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:&quot;The Story So Far&quot;,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="The Story So Far" title="The Story So Far" srcset="https://substackcdn.com/image/fetch/$s_!gfma!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 424w, https://substackcdn.com/image/fetch/$s_!gfma!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 848w, https://substackcdn.com/image/fetch/$s_!gfma!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!gfma!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc70ff22f-a2ab-45a9-973b-126d878201a2_2000x1333.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div></div></div></a></figure></div><p>About five years ago, I decided I wanted to start a business. I wasn&#8217;t sure what it would be. Ideas came up but I was never committed to them. Because I could not commit, no meaningful work was being done.</p><p>I eventually decided that I would like to help my wife. Well, I had decided a while back, but she has only recently warmed to the idea. She is a lawyer who often deals with family law related matters.</p><p>Up until today, the steps I have taken to start a business have been reading in an attempt to comprehend what exactly I need to do and what it is that I am making.</p><h3>What I know so far</h3><p>All of the business learning comes down to these facts:</p><ul><li><p>A business is a series of systems and processes that receive, change, create, and provide value from/to customers, employees, and partners. A map of this is called a business model.</p></li><li><p>In this context, value can mean many things: money, information, services, products, or property that helps the customer, employee, or partner make some meaningful progress towards a goal.</p></li><li><p>You are not a business. As such, you may work the jobs inside of the business but you also must work on the business to develop those systems and processes.</p></li><li><p>To work on those systems and processes, you have to have a process. The scientific method shines here:</p><ul><li><p>Write a hypothesis</p></li><li><p>Create an experiment</p></li><li><p>Perform the experiment</p></li><li><p>Analyze the response</p></li><li><p>Update your system or process based on what you learned.</p></li></ul></li><li><p>The best results for those experiments requires you to remove variables and biases. Customers do not exist in a lab, though, unless you sell scientific equipment. You have to avoid inserting your own bias into the experiment.</p></li></ul><h3>What I need to do still</h3><p>One of the books I am reading at the moment is The Startup Owner&#8217;s Manual. In it, Steve Blank proposes a breakdown of businesses into two stages, which each of those having a series of sub-stages and sub-sub-stages.</p><ul><li><p>Customer Development: Searching for a scalable business model involves</p><ul><li><p>Customer Discovery: Searching for a model (problem/solution fit)</p><ul><li><p>Stating your hypotheses</p></li><li><p>Testing the problem</p></li><li><p>Testing the solution</p></li></ul></li><li><p>Customer Validation: Making sure it is scalable (product/market fit)</p><ul><li><p>Initial Positioning</p></li><li><p>Selling to Earlyvangelists</p></li><li><p>Updating Positioning</p></li></ul></li></ul></li><li><p>Business Execution: Executing a business model involves both</p><ul><li><p>Customer Creation: Growing the company</p></li><li><p>Company Building: Maintaining the company</p></li></ul></li></ul><p>So, I can say that I will be searching for a business model over the next few months, or possibly longer. Further, after I find one I need to validate it.</p><p>The Startup Owner&#8217;s Manual makes a clear distinction between physical products and digital products (which it refers to as web/mobile products.) They take different routes for some steps. I&#8217;m not 100% this is always the case. It seems to me that, with a finite and probably quite small list of potential customers for a SaaS tool, I might be better off contacting them directly, more similar to a physical product.</p><p>Either way, I&#8217;m going to attempt to do Customer Discovery. I&#8217;m going to do it as close to the book as I can. My goal is to start doing customer interviews by the end of the month.</p><p>For the interview I have the following tasks:</p><ol><li><p>Write down all hypotheses</p></li><li><p>Figure out which hypothesis to disprove</p></li><li><p>Figure out what I need to learn in the interview to disprove it</p></li><li><p>Figure out who to interview</p></li><li><p>Schedule the interview</p></li><li><p>Prepare for the interview</p></li><li><p>Have the interview</p></li><li><p>Learn something from the interview</p></li></ol><p>Currently, I'm about 1/10th of the way done the first task. I live a pretty busy life. I can barely get time to clarify my thoughts. It doesn&#8217;t make any sense to be anything other than as efficient as possible.</p><p>This will be difficult.</p>]]></content:encoded></item><item><title><![CDATA[Time for Something New]]></title><description><![CDATA[I've had a blog on Medium for ages.]]></description><link>https://www.jakew.ca/p/time-for-something-new</link><guid isPermaLink="false">https://www.jakew.ca/p/time-for-something-new</guid><dc:creator><![CDATA[Jake Winters]]></dc:creator><pubDate>Sat, 12 Nov 2022 01:19:13 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!k5tm!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcf66df35-58be-4040-94bc-08d971e90917_1282x1284.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I've had a blog on Medium for ages. And I still plan to keep it. It is meant for Software Development, but this blog is meant for something new.</p><p>For the past five years, I've been infatuated with the idea of starting a business. Over the next few years, I plan to do so and document the entire process on this blog. For those that are not familiar, "Build in Public" is the term for when an entrepreneur shares their process online, including their ups and their downs.</p><p>In the next article, I'm going to write up where I am at. It may get pretty long.</p>]]></content:encoded></item></channel></rss>