Startup Therapy

In today’s Startup Therapy Podcast, Wil and Ryan talk about putting every down for a much needed break. No, you can’t say, “I can’t take a break yet.” Or say, “Your hands are tied at the moment.” It’s critical that you take a break in between milestones, unless you want to get stuck on productivity and run dry on creativity.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:24 When will you take a break? 05:08 Find milestones to fit in long-term breaks 10:37 Founders excel at planning but terrible at taking a break 13:41 When your only milestone to take a break is getting sick 18:59 If you recharge, you can do more work 22:48 The golden periods of creativity and analytical productivity 24:10 Get off, reset, and get back on with maximum energy 28:40 Some people aren’t taking PTOs 32:20 The concept of multiplicity 33:

In today’s Startup Therapy Podcast, Wil and Ryan talk about focusing on what you are trying to achieve before taking action on any big ideas you might have. Some of these ideas don't necessarily lead you to where you want to go. Some, if pursued, just end up in failures and frustrations. Instead, focus on where you want to go and then figure out how you want to get there.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:24 Getting stuck in looking or working on an idea 03:41 Your business idea should align with what you love to do 06:46 Aspirations change as we age 11:00 Making a business out of something you’re good at 17:59 Specific goals makes it easy to map things around it 23:05 Every founder knows what to avoid 27:21 Just stop doing things that make you unhappy 31:29 When you’re using the wrong yardstick to m

In today’s Startup Therapy Podcast, Wil and Ryan talk about how increasing your staff does not necessarily mean growth, but a deliberate liability. Many people just focus on increasing the number of their employees and do not think about the cost of hiring more people. Yes, you need more people to get work done faster. Yes, you need additional minds to pitch in new ideas. But what if your revenue is lower than the liabilities? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:39 Some people use staff count as a measure of success 03:40 A growing staff is only seen as a progress 07:01 Management strain continues as you add more people 10:48 There’s a diminishing return in every additional hire 14:28 Each new person that comes in is a burden in some form 16:08 Why do we associate hiring people with growth? 20:11 Puttin

In today’s Startup Therapy Podcast, Wil and Ryan talk about the dues founders pay for neglecting their health. Pushing yourself too much, putting your body through so much pressure, and then ignoring the warning signs as they come, you’re unconsciously trading your life for the success of your company. Don’t curse yourself in the process!  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:43 When you’re running your life too fast, you’re sacrificing your health 07:50 Processing all of life by not processing it 14:26 Because your body can adapt to anything, you shrug off any symptom 18:07 Early in our careers, we’re not aware of these problems 21:38 Founders rarely have a support structure 25:09 We're responsible for the conditions that created the liabilities 27:18 It’s difficult to admit you’re wrong when you made t

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens when things work for everyone else but not for you. The effort founders put into our Startup is a sacrifice in all forms and shapes, to the extent of spending less time with family, neglecting our health, or even getting a pay cut just to keep the business rolling. Yes, you are the founder but you’ve become a slave to your own business. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:11 Things are going great for everyone except for you 04:20 Concepts that led to you being a founder 07:17 We're essentially mortgaging our goals without realizing it 12:36 When we take an investor, the investor becomes our boss 15:32 You need to set goals that are unchangeable 21:24 There is a threshold where commitment becomes destructive 26:12 It’s disruptive when

In today’s Startup Therapy Podcast, Wil and Ryan talk about changing a person’s personality (or the attempt to do so). It’s one of the factors founders cannot control and it’s silly to keep telling the same person what they should be doing more than once. It’s a waste of energy, a waste of time, and definitely a lost cause. Put your time and effort into someone else!Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:22 Trying to enforce behavioral change in your people 04:32 Them being a jerk is just reflection of our bad leadership  08:40 Skills: the things you can do, Personality: the things you can’t do 11:59 We keep thinking that we are the solution to the problem 16:54 Set an environment with a healthy culture people can mimic 20:56 Do not allow performance to outweigh the emotional wellbeing of the business 23:03 W

In today’s Startup Therapy Podcast, Wil and Ryan talk about burnout when you’re nearly at the end of your Startup journey. Every sacrifice and risk you’ve taken will become useless if you feel tired and decide to take a break at the most crucial time and that’s when you’re at the last step of closing the deal. The trick is to surround yourself with people who will help you get through this phase. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:55 What happens when we’re near the end of the deal? 05:53 Startup equity is the most expensive currency one can spend 09:31 When you just want to be done with it 11:56 What else can you do to motivate yourself? 17:54 Being vulnerable at this stage doesn’t allow for a second chance 20:21 What happens if you fall apart at the last moment? 24:53 Every hardship loses value if you d

In today’s Startup Therapy Podcast, Wil and Ryan talk about avoiding unpleasant breakups. There always comes a time when you need to part ways with people, friends, staff, even investors. Every bad breakup can seriously damage your reputation in any means possible simply because some harbor vindictive emotions and speak negatively against you. What can you do then to avoid that? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:22 How many good stories do you remember of breakups throughout your career? 03:55 Your poor actions is what people remember the most 06:21 Letting go of people means having more than one conversation 12:42 Your reputation takes years to build and takes seconds to destroy 17:23 The damage a single blown relationship can do 22:41 How handle breakups that usually end well 25:10 The need to justify

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens after you sell your Startup. Beyond the big paycheck that will certainly make your life better, is the lingering attachment you have for your company and what becomes of it after you give up ownership and control over it. And what about the employees you’re leaving behind? Will they be well taken care of?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:40 This fantasy of reaching this level when you want to sell your Startup 05:35 When you sell, how is everyone else in the organization affected? 08:59 From the one making the decisions to asking permission from someone else 14:01 Realizing that you have to step off the trail is a tough pill to swallow 17:51 It won’t be the same environment and a lot of people won’t stick around 23:26 This is about

In today’s Startup Therapy Podcast, Wil and Ryan talk about power struggle. A lot of us are used to hearing people telling us what we should and shouldn’t do, what we can and cannot achieve just because these people have tried it or have been in a similar situation. What they don’t realize though is the difference in capacity and skills. What works for them may not work for you, and what works for you didn’t work out for them.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:27 The value in having a level of power and control in an agency 02:45 When having somebody else determine your destiny wasn't going to work for you 11:01 Setting your own path and not allowing anyone to tell you what to do 16:36 Stop listening to what everybody else is telling you to do 23:31 If you can do it once, you can do it again 27:10 What if

In today’s Startup Therapy Podcast, Wil and Ryan talk about regret. Founders are bound to make decisions all the time. These decisions can make or break the Startup, and this is why regret is inevitable. Not all decisions bring a positive outcome, and when the outcome is the opposite of what you had anticipated, it’s part of the risk you’re taking. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:33 Can you remember the first time you felt regret during a trade off? 05:15 The regret didn’t kick until later 07:43 Many of the risks that we’re putting up won’t return 11:39 We assume that we can make up for these risks 14:09 Don’t use the same pattern whenever you experience something new 17:28 When we form habits, we stop thinking about the different outcomes 21:32 Myth: No matter what the sacrifice is, you’ll be able to

In today’s Startup Therapy Podcast, Wil and Ryan talk about how we get blinded by the early signs of growth. When things go well, we tend to think it’s the golden moment and that your Startup is on it’s way to getting big, only to find out a week or a month later that you’re back at step one. Early stage successes become dangerous when we get blinded by them and start making the wrong decisions.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:20 Early signals that tend to blind us from what we actually should be doing 04:54 It becomes dangerous when we start making decisions based on sudden growth 08:41 When things go well, it increases our vulnerability to make the wrong decisions 14:23 Yes, it’s going well, but you aren’t making any profit 19:24 It’s a mentality problem when we get too excited at the early stages 23:

In today’s Startup Therapy Podcast, Wil and Ryan talk about when is the best time to sell your Startup. It’s a tedious process so you shouldn’t just focus on what’s happening during the negotiations but also the pros and cons after the sale is made. And of course, how much you’re being paid for selling is as important as HOW you’re getting paid. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:11 “What happens if I sell too early?” 06:36 Buyers are often negotiating to pay for a company’s future value 10:17 Whatever cash you’re taking now might be the last cash you’ll ever get in the negotiations 15:10 It’s not about how much but HOW you’re getting paid 17:58 Myth: The maximum amount the company is worth is equal to how much the founder need 27:21 You have to be realistic that you might not be able to sell

In today’s Startup Therapy Podcast, Wil and Ryan talk about going back to an office setting. The idea that more work gets done inside the office is no longer as effective as it used to be. An office setting may not be that substantial anymore for Startups. A lot of businesses are being run remotely and by far, they are progressing well.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:28 What happens when we return to our offices? 04:15 In current times, is an office really necessary? 08:47 Myth: We need an office to build culture 15:59 An office is the least likely way to build friendships 23:37 Myth: We need an office to get work done 27:20 Office equals work is no longer true 30:36 Slack and other project management tools can make collaborations happen 35:25 Collaboration versus coordination

In today’s Startup Therapy Podcast, Wil and Ryan talk about the notion that your current success will be the same for every Startup you build. While you’re in the momentum and when new ideas come in, you’re most likely tempted to venture into another Startup. Right? But, take a pause there and consider the odds of your success.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:25 The notion that your current success will be lifetime 04:59 We think about our startup success the way people tend to think about career success 08:05 Sometimes, founders are just done and want to sell fast 14:36 We optimize for cost and revenue over time but unwilling to invest time when it’s over 18:28 We love to assume the outcome in that next hand and just carry forward 22:56 Stick around and work on every angle to achieve exponential lift

In today’s Startup Therapy Podcast, Wil and Ryan talk about founders allowing open discussion of socio-political issues inside the workplace. Over the years, societal and political issues are topics that can either encourage healthy discussions and debates within the team or instigate friction and divide within the company. The question is, HOW do we talk about these issues? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:25 Socio-political issues in a workplace 03:02 It’s important how and where we talk about these issues 05:55 Areas where we can start to have more productive conversations 10:51 Focus has a cost and it’s not that simple 14:44 Some socio-political issues are directly impacting people’s focus 11:39 18:03 Not all founders really care about other people’s issues outside of work 20:28 There are a lot of p

In today’s Startup Therapy Podcast, Wil and Ryan ask, is it too early to get an advisor? Many Startup companies invest in an advisor to tap into connections that can possibly help raise additional capital. Yet, this investment does not promise successful returns because some introductions don’t end with the results founders are hoping for. The anticipated business meetings are never set.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:28 How often were you asked to be a business advisor? 03:55 What's the guarantee that they want to know you? 07:08 If getting an advisor is just for raising the capital 09:31 One-sided conversations: what’s the biggest thing you can have getting an advisor 12:10 What if you make the introductions and nothing comes of it? 16:18 Ponder first if it’s the right time to invest in an investor 1

In today’s Startup Therapy Podcast, Wil and Ryan talk about at what cost Startups are built on. What people often see is it’s all about raising money and getting external financial support, that additional funds are more than enough to keep the business going. But what people don’t see is the physical, mental, and emotional health that are being spent alongside a bloating debt. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:24 The true currency spent when building a Startup 05:10 What are the personal costs for the founders? 09:05 Raising more money doesn’t make things any easier 19:31 Our Startups pull our health on different directions 23:58 Founders slowly lose connection with close relationships 29:00 Are you doing better than before you started your business? 33:13 If you’re well-being is failing, your Startup s

In today’s Startup Therapy Podcast, Wil and Ryan talk about imaginary debt. A lot of founders are tied to this idea that employees will commit the same level of sacrifice as they would for the company. And that people will appreciate what they do and stick around no matter what happens. But it’s all an illusion. No one can actually match a founder’s willingness to sacrifice everything for the Startup. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:48 When you feel indebted to the people in your team 06:26 Your team’s sacrifice is exponentially different from yours 09:43 Everyone else is going to be looking out for themselves 13:23 Founders find it difficult to get out of unhealthy situations 17:26 There is a point at which feeling indebted has a limit 20:28 No one actually takes care of the founders 25:27 The endless

In today’s Startup Therapy Podcast, Wil and Ryan talk about the most dreaded outcome - a failing Startup. When a business fails, founders often wallow over how people react and what they can say about the situation. The adverse reactions don’t matter. What should matter is who stays to help pull you out of the rubble.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:19 Understanding how founders feel when a Startup fails 05:44 When you can’t deal with how people will process the failure 10:22 The Steve Jobs interview and dealing with criticisms 12:05 Do the people you’re concerned about actually have a voice in the situation? 17:14 Only founders who failed can sympathize with you 21:47 Surround yourself with people who knows what you’re going through 25:45 As a founder, how do you reach out? 29:58 When one founder is