With all the doom and gloom of the past few months and all signs pointing to hard times ahead, I’ve been thinking back to earlier in the decade, during the dotcom bust.

I was at Live365, the Internet radio network, and we had burned through millions of dollars with no appreciable revenues nor a business model. Our CEO/founder had left, and I found myself promoted to the management team well short of my 30th birthday and with no management experience to speak of.  Our investors, having lost faith in the prior management team, had the Company on a very tight leash.  So tight that we depended on a wire transfer every two weeks to meet payroll and other obligations.

At one point, our ISP shut us off, and we had no Internet access at the office. I had to get an employee to drive a check over so that they would turn us back on. Even worse, our site went down when the people we bought bandwidth from got shut off themselves. It wasn’t our fault, but we were still down, and the worst part was that we didn’t have enough cash to migrate to another bandwidth provider. I’ll never forget one of our employees offering to make the Company a personal loan. I couldn’t accept it because I wasn’t sure if we’d be able to pay him back.

Amazingly, our users didn’t give up on us. They set up alternate forums to discuss what was going on, sent pizza to our offices and, most importantly, gave us moral support. I won’t go through the litany of hardship we faced but, suffice to say we almost went under a few times. We were able to survive through sheer will, the dedication of our employees and users and a lot of luck.  There were so many lessons learned, but, in particular:

1. Be as transparent with your employees and other stakeholders as you can be. At one point, we had to tell everyone in the company that coming to work was optional and that the next payroll was in doubt because of our cash issues. Even though it was bad news, they appreciated the transparency. In hindsight, I would have been much more communicative than I had been.

2. Cultivate a trusted adviser or mentor outside of the workplace. I think people should do this anyway but it helped me a great deal to have someone I could talk to about the issues I was facing and dispassionately help me evaluate the scenarios and available options.

3. Remember whom you work for and where your fiduciary duties lie. Yes, you ultimately work for yourself.  But, as a founder or management team member, you may have fiduciary duties to shareholders, both common and preferred, to employees, creditors and customers.  Their interests can diverge even in the best of times and especially so when things start going pear-shaped. I made some painful decisions that ruined a friendship but were for the ultimate good of the company and satisfied my fiduciary and ethical obligations — and, to reiterate No. 2 above, I’m glad I had a trusted adviser to help me make sense of things during such an emotionally fraught period.

4. Accelerate non-advertising revenue models. This is a more practical recommendation.  Even if your usage and advertising metrics are growing nicely, now is the time to accelerate development of non ad-based models and prioritize the other revenue streams more highly.  Your investors and poptential investors and acquirers will appreciate this. Not only that but they are likely to discount your ad-based revenues anyway, so any momentum you can show outside of ads will bolster your story.

5. What doesn’t kill you will only make you stronger. Easy to say, hard to live through. But just keep telling yourself this when things really, really suck.

6. Pray! Seriously, luck plays a big role. Do whatever you can to make your own luck.

While it’s going to be a bumpy road ahead that will involve a lot of pain for many people, I think it actually will be better this time around: The Internet, the web and mobile are real media with real users, real revenues and real business models. Add to that the fact that it’s orders of magnitude cheaper to develop and go-to-market than it was then, and I don’t think the downturn in our general field will be as drastic as it was back in the day.

Raghav “Rags” Gupta is VP of International Partnerships at Brightcove, where he has worked since 2005. His blog can be found at www.ragsgupta.com.

With all the doom and gloom of the past few months and all signs pointing to hard times ahead, I’ve been thinking back to earlier in the decade, during the dotcom bust.

I was at Live365, the Internet radio network, and we had burned through millions of dollars with no appreciable revenues nor a business model. Our CEO/founder had left, and I found myself promoted to the management team well short of my 30th birthday and with no management experience to speak of.  Our investors, having lost faith in the prior management team, had the Company on a very tight leash.  So tight that we depended on a wire transfer every two weeks to meet payroll and other obligations.

At one point, our ISP shut us off, and we had no Internet access at the office. I had to get an employee to drive a check over so that they would turn us back on. Even worse, our site went down when the people we bought bandwidth from got shut off themselves. It wasn’t our fault, but we were still down, and the worst part was that we didn’t have enough cash to migrate to another bandwidth provider. I’ll never forget one of our employees offering to make the Company a personal loan. I couldn’t accept it because I wasn’t sure if we’d be able to pay him back.

Amazingly, our users didn’t give up on us. They set up alternate forums to discuss what was going on, sent pizza to our offices and, most importantly, gave us moral support. I won’t go through the litany of hardship we faced but, suffice to say we almost went under a few times. We were able to survive through sheer will, the dedication of our employees and users and a lot of luck.  There were so many lessons learned, but, in particular:

1. Be as transparent with your employees and other stakeholders as you can be. At one point, we had to tell everyone in the company that coming to work was optional and that the next payroll was in doubt because of our cash issues. Even though it was bad news, they appreciated the transparency. In hindsight, I would have been much more communicative than I had been.

2. Cultivate a trusted adviser or mentor outside of the workplace. I think people should do this anyway but it helped me a great deal to have someone I could talk to about the issues I was facing and dispassionately help me evaluate the scenarios and available options.

3. Remember whom you work for and where your fiduciary duties lie. Yes, you ultimately work for yourself.  But, as a founder or management team member, you may have fiduciary duties to shareholders, both common and preferred, to employees, creditors and customers.  Their interests can diverge even in the best of times and especially so when things start going pear-shaped. I made some painful decisions that ruined a friendship but were for the ultimate good of the company and satisfied my fiduciary and ethical obligations — and, to reiterate No. 2 above, I’m glad I had a trusted adviser to help me make sense of things during such an emotionally fraught period.

4. Accelerate non-advertising revenue models. This is a more practical recommendation.  Even if your usage and advertising metrics are growing nicely, now is the time to accelerate development of non ad-based models and prioritize the other revenue streams more highly.  Your investors and poptential investors and acquirers will appreciate this. Not only that but they are likely to discount your ad-based revenues anyway, so any momentum you can show outside of ads will bolster your story.

5. What doesn’t kill you will only make you stronger. Easy to say, hard to live through. But just keep telling yourself this when things really, really suck.

6. Pray! Seriously, luck plays a big role. Do whatever you can to make your own luck.

While it’s going to be a bumpy road ahead that will involve a lot of pain for many people, I think it actually will be better this time around: The Internet, the web and mobile are real media with real users, real revenues and real business models. Add to that the fact that it’s orders of magnitude cheaper to develop and go-to-market than it was then, and I don’t think the downturn in our general field will be as drastic as it was back in the day.

Raghav “Rags” Gupta is VP of International Partnerships at Brightcove, where he has worked since 2005. His blog can be found at www.ragsgupta.com.

Call it a coincidence, but over the past few days I have spent a lot of time with folks who used to work for Amazon but are now out doing new things. It all started with Jason Kilar, the CEO of Hulu, who was a keynote speaker at our NewTeeVee Live conference. Then last night I met with Dave Schapell, founder and CEO of TeachStreet, an e-marketplace for teachers. And this morning I had coffee with Jeff Lawson, co-founder of Twilo.

My buddy Dave McClure was the one who pointed out that they are all part of the Ex-Amazon club. Just like the rising number of ex-Google entrepreneurs I wrote about last year, these guys are leaving top jobs at one of the best technology companies in the U.S. Here is a list of just some of those names, their current companies and their previous positions at the e-tailer:

• -Jeff Holden, CEO and co-founder, Pelago (Amazon consumer web sites)
• -Michael Sha, co-founder, WikInvest (Amazon Payments)
• -Dave Schappell, CEO and founder, TeachStreet (Misc.)
• -Vikas Gupta, co-founder, Jambool (Amazon Flexible Payment Systems)
• -Reza Hussein, co-founder, Jambool (Mechanical Turk)
• -Jeff Lawson, co-founder, Twilio (Amazon Web Services)
• -Keith Schorsch, CEO and founder, Trusera (Misc.)

Plus Jason Kilar, CEO of Hulu (Amazon Marketplace)

Now this isn’t even a comprehensive list, and slowly and surely, it is expanding. The easy availability of capital in Seattle certainly helps, but more importantly it speaks to the amount of top-quality talent that Amazon has been able to attract over the years. Lawson, who stopped by for a cup of tea this morning to pitch his company, Twilio, said that one of Amazon’s biggest strengths has always been its ability to recruit and hire great minds.

It is because of this hiring policy that the company has not only stayed ahead of the technology curve, but established itself as the leader in Web 2.0 innovation. That’s in stark contrast to other tech giants such as Yahoo and Google, which have instead taken their cues from small startups. For talented people, the allure of working with Jeff Bezos can be what clinches the deal, according to Schappell of TeachStreet, which counts Bezos Expeditions as one of its investors. His company has essentially developed a place where you can go to find things like a French teacher, or someone to give you trombone lessons. I like to call it the Yellow Pages with brains, and it’s the kind of service a company like eBay should have launched instead of mucking around with things like Skype.

Those who know Bezos well say that he isn’t afraid of losing and wants to win big — and that means making big bets. This “nothing-in-the-middle” attitude is particularly attractive to folks with an entrepreneurial gene.

Of course, it also has its downside. Bezos’ big-play approach frustrates those who want to unleash small ideas, and nurture them over a period of time. Eventually some great people couldn’t live within the corporate structure of Amazon and went on to do their own thing. Like Lawson, who until recently was the CTO of Stubhub before starting Twilio, a company that has developed an easy way for web application developers to add voice capabilities to their offerings using standard web-programming techniques.

Should Amazon be worried about this brain drain? Absolutely not, for the company continues to attract talent the way lights attracts moths. I’ve often wondered what Amazon would do next, and I have a few ideas as to where I think they’re going. Someday I’ll blog about that, too.

Check out my video interview with Jeff Bezos.

Call it a coincidence, but over the past few days I have spent a lot of time with folks who used to work for Amazon but are now out doing new things. It all started with Jason Kilar, the CEO of Hulu, who was a keynote speaker at our NewTeeVee Live conference. Then last night I met with Dave Schapell, founder and CEO of TeachStreet, an e-marketplace for teachers. And this morning I had coffee with Jeff Lawson, co-founder of Twilo.

My buddy Dave McClure was the one who pointed out that they are all part of the Ex-Amazon club. Just like the rising number of ex-Google entrepreneurs I wrote about last year, these guys are leaving top jobs at one of the best technology companies in the U.S. Here is a list of just some of those names, their current companies and their previous positions at the e-tailer:

• -Jeff Holden, CEO and co-founder, Pelago (Amazon consumer web sites)
• -Michael Sha, co-founder, WikInvest (Amazon Payments)
• -Dave Schappell, CEO and founder, TeachStreet (Misc.)
• -Vikas Gupta, co-founder, Jambool (Amazon Flexible Payment Systems)
• -Reza Hussein, co-founder, Jambool (Mechanical Turk)
• -Jeff Lawson, co-founder, Twilio (Amazon Web Services)
• -Keith Schorsch, CEO and founder, Trusera (Misc.)

Plus Jason Kilar, CEO of Hulu (Amazon Marketplace)

Now this isn’t even a comprehensive list, and slowly and surely, it is expanding. The easy availability of capital in Seattle certainly helps, but more importantly it speaks to the amount of top-quality talent that Amazon has been able to attract over the years. Lawson, who stopped by for a cup of tea this morning to pitch his company, Twilio, said that one of Amazon’s biggest strengths has always been its ability to recruit and hire great minds.

It is because of this hiring policy that the company has not only stayed ahead of the technology curve, but established itself as the leader in Web 2.0 innovation. That’s in stark contrast to other tech giants such as Yahoo and Google, which have instead taken their cues from small startups. For talented people, the allure of working with Jeff Bezos can be what clinches the deal, according to Schappell of TeachStreet, which counts Bezos Expeditions as one of its investors. His company has essentially developed a place where you can go to find things like a French teacher, or someone to give you trombone lessons. I like to call it the Yellow Pages with brains, and it’s the kind of service a company like eBay should have launched instead of mucking around with things like Skype.

Those who know Bezos well say that he isn’t afraid of losing and wants to win big — and that means making big bets. This “nothing-in-the-middle” attitude is particularly attractive to folks with an entrepreneurial gene.

Of course, it also has its downside. Bezos’ big-play approach frustrates those who want to unleash small ideas, and nurture them over a period of time. Eventually some great people couldn’t live within the corporate structure of Amazon and went on to do their own thing. Like Lawson, who until recently was the CTO of Stubhub before starting Twilio, a company that has developed an easy way for web application developers to add voice capabilities to their offerings using standard web-programming techniques.

Should Amazon be worried about this brain drain? Absolutely not, for the company continues to attract talent the way lights attracts moths. I’ve often wondered what Amazon would do next, and I have a few ideas as to where I think they’re going. Someday I’ll blog about that, too.

Check out my video interview with Jeff Bezos.