Jesse interviews his friend and realtor Terry Bickmore about Terry's introduction to YNAB and how it helped transform his business and personal life. Terry offers some advice for first-time homebuyers, based on YNAB's Four Rules.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

Jesse reflects on learning to relax about spending money, especially on the "black box" line items -- unspecified purchases from Amazon that don't fit neatly into any other category, or purchases that he simply doesn't want to look up and re-categorize. Part of learning to relax about these expenditures is realizing that as long as you are achieving your primary goals -- funding an emergency fund, saving for retirement, saving for a house perhaps -- then it doesn't really matter what happens to the rest of your money. It's another way of looking at the big picture.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

The end of the year is nigh, and 2020 has been one of the most stressful in recent memory. Jesse offers some advice for those dealing with fear and anxiety during these times.   During times of fear and uncertainty, Jesse draws on Stephen R. Covey's seminal book The 7 Habits of Highly Effective People. The first habit is to be proactive and take responsibility for your reactions to events. To that end, Covey asks readers to consider their circle of influence -- What do you control? Where do you not have control? Drawing a very clear picture of your circle of influence, and defining what you don't control, can help with realizing what things you ought to be fear and what things are outside your influence, and thus should be outside your concern (or at least unworthy of spending mental bandwidth on). When people start budgeting, they often can't control what they make, but they can control some of things they spend on. So focusing on spending, giving their money a job, and following the four steps brings their attention to concrete, actionable things within their circle of influence.   Secondly, Jesse recommends learning more about the things you are fearful of. What information could you gather about a topic that would help you better understand it? If you are fearful about money, how about understanding how much you have in your checking account right now? Then take another step. What does that money need to do between now and the next time you get paid? Gathering data points and information about the things causing you fear and anxiety can help make them seem more manageable.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

Jesse and Taylor Brown, YNAB's Chief Technology Officer, celebrate the company being named Fortune's #1 Best Place to Work in Small Business in 2020. Jesse and Taylor take a walk down memory lane, reminiscing about the very early days of YNAB and how they much they've grown since, both as a company and as leaders within the business. The moniker "best place to work" doesn't just happen, but rather is a consequence of Jesse and Taylor's work in defining their company and employee values and consistently acting on those principles over the years.   Of course winning this honor is due to the work of everyone at YNAB, especially the operations team (lead by COO Chance Gurr) whose responsibility is making sure YNAB is a rewarding place to work. So, Jesse and Taylor wish to thank everyone at YNAB for their hard work and for embodying the company's values every day.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

Jesse sits down with acclaimed finance writer and entrepreneur Ramit Sethi for a long chat about the mindset of financial success, how to think like an entrepreneur, and why the most important question about personal finance you need to be able to answer is... "Why?".   Ramit is the author of the 2009 New York Times Best Seller, I Will Teach You to Be Rich, and the founder of Earnable, a community of entrepreneurs in which he coaches people how to think like entrepreneurs, develop viable business ventures, and market effectively to grow their business.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

Jesse interviews wellness expert, educator, and entrepreneur Robyn Conley Downs about applying her strategies for wellness to making lasting change in budgeting.   You can find Robyn here: Real Food Whole Life: https://realfoodwholelife.com/about/ IG: @realfoodwholelife   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

In the world of cost accounting, there's a concept known as contribution margin. Basically, it's how much you make on a product or service after you consider how much it cost to make that thing. The formula is revenue less the variable costs that go into making the product. Contribution margin is an important metric for businesses because it tells you whether you are making a profit on the things you sell. After all, it would do no good to sell a bunch of t-shirts for $18 a piece, if each of them costs you $20 to make!   Now, Jesse asks, what if we apply this concept to our life? We have jobs that earn us revenue. What do they cost to do? Time, obviously, but perhaps also driving/commuting, stress? The point is, the things that earn us money have a non-zero cost associated with them, and it's wise to keep track of that cost and make sure, at the end of the day, that we are using our time in a profitable manner.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

It's not a dirty word, so let's say it together -- wealth! At YNAB, we often use the words "save money," and it's a more approachable concept, something that seems achievable in the short term. Wealth can seem like such a far-off concept sometimes. But at the end of the day, that's what we're all trying to do, is to build wealth that will allow us to do more of what we want to do in life.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

While canning tomatoes from a bumper crop, Jesse realized the process was going to take a looooooong time. His wife advised him, simply, to "just settle in." Anything that yields great results in the future takes both upfront effort and perseverance. Whether it's gardening, putting up vegetables for the winter, or budgeting, you have to settle in.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com

Jesse lays out a strategy for managing unknown expenses without continually dipping into your emergency fund. Traditional budgeting advice tells you to create an emergency fund for dealing with unforeseen expenses, but often people end up using their emergency funds for irregular, but foreseeable expenses -- things like new tires, new cars, A/C repair, etc. They don't happen regularly, maybe only every several years, but if you look into the future you know they are coming.   For YNAB'ers that are following Rule #2, Embracing Your True Expenses, these aren't true emergencies, and they are already covered in the budget. In the rare event of a true emergency that catches you off guard, Jesse recommends that rather than spending money out of your global emergency fund, set up a new category for that expense. Maybe it's a house repair that you had never encountered before. Make a new category for that type of repair, and start a new sinking fund for it like you do for other Rule #2 expenses.   Over time, this strategy will give you useful data about your true expenses, so that you can be more prepared for next time.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com